Standard Article

Functionalization of Carbohydrates in Water

Part 5. Reactions in Water

  1. Marie-Christine Scherrmann1,
  2. André Lubineau1,
  3. Yves Queneau2,3

Published Online: 15 JUL 2010

DOI: 10.1002/9783527628698.hgc056

Handbook of Green Chemistry

Handbook of Green Chemistry

How to Cite

Scherrmann, M.-C., Lubineau, A. and Queneau, Y. 2010. Functionalization of Carbohydrates in Water. Handbook of Green Chemistry. 5:10:291–330.

Author Information

  1. 1

    Université Paris-Sud 11, Institut de Chimie Moléculaire et des, Matériaux d'Orsay, CNRS UMR 8182, Laboratoire de Procédés et Substances Naturelles, Orsay, France

  2. 2

    INSA-Lyon, Laboratoire de Chimie Organique, Villeurbanne, France

  3. 3

    Université Lyon 1, Institut de Chimie et Biochimie, Moléculaires et Supramoléculaires, INSA-Lyon, CNRS, UMR 5246, CPE-Lyon, Bâtiment CPE, Villeurbanne, France

Publication History

  1. Published Online: 15 JUL 2010

Chemistry Terms

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Abstract

Carbohydrate chemistry and chemistry in water go well with each other for three main reasons. First, the synthesis of carbohydrate derivatives of biological relevance has profited from the advances in the use of aqueous media as solvents, leading to new compounds with improved reactivity and selectivity. Second, carbohydrates, being water soluble, have been used as water solubility inducers for water-promoted reactions. Third, part of the chemistry devoted to the use of carbohydrates as raw materials, as an alternative to fossil resources, is performed in water. Indeed, it is now strategic to combine different key principles of green chemistry, namely the use of clean solvents and the use of renewable starting materials in synthetic chemistry. Moreover, it can be connected with the design of new derivatives with improved environmental properties. The chapter focuses on the chemistry of small carbohydrates (not polysaccharides), reviewing C[BOND]C bond formation reactions involved in multi-step syntheses of complex structures or in direct processes towards functional derivatives, C[BOND]N and C[BOND]O bond formation reactions. The latter aspect, which deals with the reactivity of sugars as polyols, is an extremely large topic, and for reasons of conciseness the main issues of this chemistry will be illustrated by focusing on the example of sucrose, the most available small carbohydrate. Also, some approaches in which a carbohydrate serves as a polar appendage which provides the water solubility necessary to take advantage of hydrophobic effects are described, in addition to the use of aqueous solutions of sugars as media in which hydrophobic effects are intensified.

Keywords:

  • carbohydrates;
  • water;
  • functionalization;
  • C-glycosides;
  • renewable resources;
  • sucrose;
  • green chemistry

Featured Compounds

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  1. 1 - 144
Compound 1b
Molecular Weight:128.0862
Molecular Formula:C4H4N2O3
InChIKey:HNYOPLTXPVRDBG-UHFFFAOYSA-N
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Compound 1a
Molecular Weight:156.1393
Molecular Formula:C6H8N2O3
InChIKey:VVSASNKOFCZVES-UHFFFAOYSA-N
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Compound 2a
Molecular Weight:340.2617
Molecular Formula:C12H17N2NaO8
InChIKey:KLWZUHFYBJBGJL-MWAMCEPPSA-M
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Compound 2b
Molecular Weight:312.2086
Molecular Formula:C10H13N2NaO8
InChIKey:VRYMLKBPTYSJGV-HUQPTLPOSA-M
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Compound 3a
Molecular Weight:340.2617
Molecular Formula:C12H17N2NaO8
InChIKey:KLWZUHFYBJBGJL-WOQWRVJUSA-M
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Compound 3b
Molecular Weight:312.2086
Molecular Formula:C10H13N2NaO8
InChIKey:VRYMLKBPTYSJGV-RHYLFIMGSA-M
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Compound 4a
Molecular Weight:340.2617
Molecular Formula:C12H17N2NaO8
InChIKey:KLWZUHFYBJBGJL-JYZXNKRMSA-M
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Compound 4b
Molecular Weight:312.2086
Molecular Formula:C10H13N2NaO8
InChIKey:VRYMLKBPTYSJGV-SAXFKDPRSA-M
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Compound 5a
Molecular Weight:339.277
Molecular Formula:C12H18N3NaO7
InChIKey:KLUWWLIZIHUBQG-QVYHMGMLSA-M
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Compound 5b
Molecular Weight:311.2238
Molecular Formula:C10H14N3NaO7
InChIKey:BPBIXTGPIDOLCC-FMTWABNXSA-M
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Compound 1
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 6
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 7
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 9
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 8
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 10
Molecular Weight:243.2564
Molecular Formula:C11H17NO5
InChIKey:OTGHXPARZDXDIM-GMTAPVOTSA-N
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Compound 11
Molecular Weight:140.1797
Molecular Formula:C8H12O2
InChIKey:BADXJIPKFRBFOT-UHFFFAOYSA-N
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Compound 12
Molecular Weight:254.279
Molecular Formula:C13H18O5
InChIKey:FVOXNKMQQXREPX-BXKDBHETSA-N
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Compound 13
Molecular Weight:394.4587
Molecular Formula:C21H30O7
InChIKey:BBUHQVMMBBHAFA-DPMMWBKBSA-N
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Compound 16
Molecular Weight:284.2382
Molecular Formula:C11H17NaO7
InChIKey:HTJZJGUHGRORPP-KPMYGZRYSA-M
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Compound 21
Molecular Weight:382.3603
Molecular Formula:C15H26O11
InChIKey:CZPVHXTZZCIQGE-QNOHERNSSA-N
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Compound 18
Molecular Weight:220.2197
Molecular Formula:C9H16O6
InChIKey:XMNOVTHWCLGVID-XDQCBXAXSA-N
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Compound 19
Molecular Weight:220.2197
Molecular Formula:C9H16O6
InChIKey:XMNOVTHWCLGVID-QKAWAISNSA-N
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Compound 20
Molecular Weight:382.3603
Molecular Formula:C15H26O11
InChIKey:CZPVHXTZZCIQGE-VYDBGKAKSA-N
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Compound 22
Molecular Weight:261.2717
Molecular Formula:C11H19NO6
InChIKey:YGBSKSJUYXEYMB-OGBGREFGSA-N
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Compound 23
Molecular Weight:261.2717
Molecular Formula:C11H19NO6
InChIKey:YGBSKSJUYXEYMB-VPJKUYQRSA-N
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Compound 24
Molecular Weight:387.3817
Molecular Formula:C17H25NO9
InChIKey:MMHNRNBIQWEFBO-BQJWPVKWSA-N
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Compound 14
Molecular Weight:302.2535
Molecular Formula:C11H19NaO8
InChIKey:HWMOVILNBDEPPR-LPGTXBCPSA-M
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Compound 15
Molecular Weight:284.2382
Molecular Formula:C11H17NaO7
InChIKey:FGOFGSBAEFDDDM-QCUZDTNBSA-N
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Compound 17
Molecular Weight:220.2197
Molecular Formula:C9H16O6
InChIKey:XMNOVTHWCLGVID-KVEIKIFDSA-N
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Compound 26
Molecular Weight:220.2197
Molecular Formula:C9H16O6
InChIKey:SZNQGAFYTSKYRU-DFTQBPQZSA-N
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Compound 27
Molecular Weight:Not Available
Molecular Formula:(CH2)nC5H8O2
InChIKey:NDOGLIPWGGRQCO-UHFFFAOYSA-N
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Compound 27a
Molecular Weight:170.2487
Molecular Formula:C10H18O2
InChIKey:WTVNFKVGGUWHQC-UHFFFAOYSA-N
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Compound 27b
Molecular Weight:212.3285
Molecular Formula:C13H24O2
InChIKey:QAXKYAIESKANJL-UHFFFAOYSA-N
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Compound 29
Molecular Weight:Not Available
Molecular Formula:(CH2)nC9H16O6
InChIKey:IHBVFLHXIHDXHD-SQXHDICFSA-N
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Compound 29a
Molecular Weight:290.3526
Molecular Formula:C14H26O6
InChIKey:BQPDRGUYCVCIDE-MEBFFEOJSA-N
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Compound 29b
Molecular Weight:332.4324
Molecular Formula:C17H32O6
InChIKey:QSHOWIXLLUYMRH-DMRKSPOLSA-N
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Compound 30a
Molecular Weight:240.3816
Molecular Formula:C15H28O2
InChIKey:OTSFAPUOIOQRCE-UHFFFAOYSA-N
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Compound 30b
Molecular Weight:324.5411
Molecular Formula:C21H40O2
InChIKey:MQJILNQGWWHNQQ-UHFFFAOYSA-N
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Compound 31a
Molecular Weight:452.4932
Molecular Formula:C20H36O11
InChIKey:ZHDWEQBIJYDSSD-GFSSERJJSA-N
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Compound 31b
Molecular Weight:494.573
Molecular Formula:C23H42O11
InChIKey:OMXFPHJEFSYKMQ-NOZMFBPCSA-N
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Compound 30
Molecular Weight:Not Available
Molecular Formula:(CH2)n(CH2)nC5H8O2
InChIKey:DGCTVLNZTFDPDJ-UHFFFAOYSA-N
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Compound 32
Molecular Weight:Not Available
Molecular Formula:(CH2O)nC3H6O3
InChIKey:YTBSYETUWUMLBZ-UHFFFAOYSA-N
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Compound 33
Molecular Weight:Not Available
Molecular Formula:(CH2O)nC6H12O3
InChIKey:UGFVKDFCBKARNH-UYMSWOSGSA-N
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Compound 34
Molecular Weight:130.1418
Molecular Formula:C6H10O3
InChIKey:Not Available
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Compound 35
Molecular Weight:118.1311
Molecular Formula:C5H10O3
InChIKey:MHGMBRBPBZPUAD-CRCLSJGQSA-N
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Compound 36
Molecular Weight:118.1311
Molecular Formula:C5H10O3
InChIKey:MHGMBRBPBZPUAD-RFZPGFLSSA-N
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Compound 37
Molecular Weight:Not Available
Molecular Formula:(CH2O)nC5H10O4
InChIKey:VRYALKFFQXWPIH-QBQQJPCDSA-N
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Compound 38
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 40a
Molecular Weight:179.012
Molecular Formula:C5H7BrO2
InChIKey:JJPZBCGMCATWNR-DUXPYHPUSA-N
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Compound 40b
Molecular Weight:241.081
Molecular Formula:C10H9BrO2
InChIKey:KELLLVPRFCIPMV-XBXARRHUSA-N
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Compound 41a
Molecular Weight:208.209
Molecular Formula:C8H16O6
InChIKey:JZGSGLXIHQVWFJ-BZCSJUTBSA-N
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Compound 41b
Molecular Weight:208.209
Molecular Formula:C8H16O6
InChIKey:JZGSGLXIHQVWFJ-GWVFRZDISA-N
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Compound 41c
Molecular Weight:208.209
Molecular Formula:C8H16O6
InChIKey:JZGSGLXIHQVWFJ-PVFLNQBWSA-N
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Compound 41d
Molecular Weight:208.209
Molecular Formula:C8H16O6
InChIKey:JZGSGLXIHQVWFJ-YQXRAVKXSA-N
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Compound 42a
Molecular Weight:210.1819
Molecular Formula:C7H14O7
InChIKey:BGWQRWREUZVRGI-XJWWOKRRSA-N
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Compound 42b
Molecular Weight:210.1819
Molecular Formula:C7H14O7
InChIKey:BGWQRWREUZVRGI-ZDMISVDFSA-N
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Compound 42c
Molecular Weight:210.1819
Molecular Formula:C7H14O7
InChIKey:BGWQRWREUZVRGI-LVUJSVCXSA-N
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Compound 42d
Molecular Weight:210.1819
Molecular Formula:C7H14O7
InChIKey:BGWQRWREUZVRGI-REBRIVGMSA-N
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Compound 39
Molecular Weight:150.1299
Molecular Formula:C5H10O5
InChIKey:PYMYPHUHKUWMLA-UHFFFAOYSA-N
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Compound 40
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 43
Molecular Weight:240.2078
Molecular Formula:C8H16O8
InChIKey:BIYJBQHXBNFTFX-BHWQZESVSA-N
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Compound 44
Molecular Weight:240.2078
Molecular Formula:C8H16O8
InChIKey:BIYJBQHXBNFTFX-LAHVLZFCSA-N
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Compound 45
Molecular Weight:240.2078
Molecular Formula:C8H16O8
InChIKey:BIYJBQHXBNFTFX-GXJZUITHSA-N
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Compound 46
Molecular Weight:280.2717
Molecular Formula:C11H20O8
InChIKey:IFAFFDXFVDAZNP-BHRXDNSCSA-N
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Compound 47
Molecular Weight:266.2451
Molecular Formula:C10H18O8
InChIKey:WFLVUYOOAGZAHX-KFUBRKPTSA-N
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Compound 48
Molecular Weight:294.2983
Molecular Formula:C12H22O8
InChIKey:KVSRSEGSJPIQOO-VPJKUYQRSA-N
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Compound 49
Molecular Weight:248.2298
Molecular Formula:C10H16O7
InChIKey:UMKGNATWHHYUEM-WUNNTHRKSA-N
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Compound 50
Molecular Weight:230.2576
Molecular Formula:C11H18O5
InChIKey:VFGWJIQTAFPNQZ-HRDYMLBCSA-N
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Compound 51
Molecular Weight:304.1883
Molecular Formula:C8H17O10P
InChIKey:AOXVGJUMSLOPNG-UFHHHNHISA-N
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Compound 52
Molecular Weight:345.2403
Molecular Formula:C10H20NO10P
InChIKey:DSSKJOUOHJGWTO-LIKBTPFBSA-N
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Compound 58
Molecular Weight:237.091
Molecular Formula:C8H13BrO3
InChIKey:FWFSAHLNAMQHAZ-XLPZGREQSA-N
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Compound 53
Molecular Weight:239.064
Molecular Formula:C7H11BrO4
InChIKey:OTYMWRUVDKNUFU-XVMARJQXSA-N
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Compound 54
Molecular Weight:237.091
Molecular Formula:C8H13BrO3
InChIKey:FWFSAHLNAMQHAZ-PRJMDXOYSA-N
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Compound 55
Molecular Weight:237.091
Molecular Formula:C8H13BrO3
InChIKey:FWFSAHLNAMQHAZ-RNJXMRFFSA-N
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Compound 56
Molecular Weight:237.091
Molecular Formula:C8H13BrO3
InChIKey:IPXLZSHBJUVKDA-XLPZGREQSA-N
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Compound 57
Molecular Weight:237.091
Molecular Formula:C8H13BrO3
InChIKey:FWFSAHLNAMQHAZ-BWZBUEFSSA-N
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Compound 59
Molecular Weight:266.2897
Molecular Formula:C14H18O5
InChIKey:DXSAHZJTYCNFEF-WYTNZGFTSA-N
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Compound 60
Molecular Weight:264.3169
Molecular Formula:C15H20O4
InChIKey:HFXBXULURRPWQY-XGUBFFRZSA-N
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Compound 61
Molecular Weight:264.3169
Molecular Formula:C15H20O4
InChIKey:HFXBXULURRPWQY-GBJTYRQASA-N
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Compound 62
Molecular Weight:264.3169
Molecular Formula:C15H20O4
InChIKey:HFXBXULURRPWQY-BYNSBNAKSA-N
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Compound 63
Molecular Weight:264.3169
Molecular Formula:C15H20O4
InChIKey:XHLHSYDZELWWFB-LQFPDLAYSA-N
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Compound 64
Molecular Weight:278.3004
Molecular Formula:C15H18O5
InChIKey:HJSVEWIQHDNLMU-XJFOESAGSA-N
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Compound 65
Molecular Weight:450.522
Molecular Formula:C24H34O8
InChIKey:BZXHEKQDRQTTMU-MTDBZWEJSA-N
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Compound 68a
Molecular Weight:898.9865
Molecular Formula:C50H58O15
InChIKey:GJZQPEXRMOCFAT-AFIYITFFSA-N
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Compound 68b
Molecular Weight:898.9865
Molecular Formula:C50H58O15
InChIKey:GJZQPEXRMOCFAT-LSNHEMQKSA-N
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Compound 66
Molecular Weight:552.6567
Molecular Formula:C35H36O6
InChIKey:KKPOREZWWWRARY-IVFJIKSYSA-N
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Compound 67a
Molecular Weight:712.8245
Molecular Formula:C42H48O10
InChIKey:VLZLKFVASTYFIJ-JWSBULTASA-N
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Compound 67b
Molecular Weight:712.8245
Molecular Formula:C42H48O10
InChIKey:VLZLKFVASTYFIJ-ZSTINCNKSA-N
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Compound 69
Molecular Weight:273.95
Molecular Formula:C6H10Br2O2
InChIKey:YRHJHRDACDTZKW-ZELZYMQXSA-N
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Compound 70
Molecular Weight:327.214
Molecular Formula:C15H19BrO3
InChIKey:GJMRIJWBIBCHGW-PAMDKOJJSA-N
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Compound 71
Molecular Weight:220.2643
Molecular Formula:C13H16O3
InChIKey:FBAOGUCJYCIZDH-RNJOBUHISA-N
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Compound 72a
Molecular Weight:202.2045
Molecular Formula:C9H14O5
InChIKey:UEMZYXSQHWVRNA-XUTVFYLZSA-N
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Compound 72b
Molecular Weight:278.3004
Molecular Formula:C15H18O5
InChIKey:HJSVEWIQHDNLMU-XJFOESAGSA-N
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Compound 72c
Molecular Weight:258.2677
Molecular Formula:C12H18O6
InChIKey:LWBFEDVQAXNLQJ-SOYHJAILSA-N
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Compound 73
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 73c
Molecular Weight:53.0626
Molecular Formula:C3H3N
InChIKey:NLHHRLWOUZZQLW-UHFFFAOYSA-N
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Compound 72
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 73a
Molecular Weight:100.1158
Molecular Formula:C5H8O2
InChIKey:JIGUQPWFLRLWPJ-UHFFFAOYSA-N
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Compound 73b
Molecular Weight:70.0898
Molecular Formula:C4H6O
InChIKey:FUSUHKVFWTUUBE-UHFFFAOYSA-N
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Compound 74
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 75
Molecular Weight:154.1632
Molecular Formula:C8H10O3
InChIKey:XQDNFAMOIPNVES-UHFFFAOYSA-N
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Compound 74a
Molecular Weight:148.1571
Molecular Formula:C6H12O4
InChIKey:FDWRIIDFYSUTDP-DUVQVXGLSA-N
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Compound 74b
Molecular Weight:148.1571
Molecular Formula:C6H12O4
InChIKey:FDWRIIDFYSUTDP-WGDKFINWSA-N
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Compound 74c
Molecular Weight:148.1571
Molecular Formula:C6H12O4
InChIKey:FDWRIIDFYSUTDP-CERMHHMHSA-N
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Compound 74d
Molecular Weight:164.1565
Molecular Formula:C6H12O5
InChIKey:PMMURAAUARKVCB-CERMHHMHSA-N
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Compound 76
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 76a
Molecular Weight:284.305
Molecular Formula:C14H20O6
InChIKey:VYUUESVROVWZQB-HSZYHJKUSA-N
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Compound 76b
Molecular Weight:284.305
Molecular Formula:C14H20O6
InChIKey:VYUUESVROVWZQB-QLAGCDLOSA-N
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Compound 76c
Molecular Weight:284.305
Molecular Formula:C14H20O6
InChIKey:VYUUESVROVWZQB-HTXZSYDESA-N
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Compound 76d
Molecular Weight:300.3044
Molecular Formula:C14H20O7
InChIKey:OJAYALVGDGFISG-LHMODEAPSA-N
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Compound 77
Molecular Weight:168.1467
Molecular Formula:C8H8O4
InChIKey:XLEYFDVVXLMULC-UHFFFAOYSA-N
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Compound 78
Molecular Weight:330.2873
Molecular Formula:C14H18O9
InChIKey:IWMUXTZLTOTAQO-MMKBDJJOSA-N
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Compound 79
Molecular Weight:492.4279
Molecular Formula:C20H28O14
InChIKey:DFBBFWZHBXXZGI-YBFIPBEFSA-N
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Compound 80
Molecular Weight:534.5571
Molecular Formula:C29H30N2O8
InChIKey:VKZWBWUZUQFABA-UHFFFAOYSA-N
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Compound 81
Molecular Weight:192.3296
Molecular Formula:C11H16OSi
InChIKey:AFFPCIMDERUIST-UHFFFAOYSA-N
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Compound 82
Molecular Weight:672.8053
Molecular Formula:C43H44O7
InChIKey:ZGMJOADIXTXWBY-IVGJHFIPSA-N
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Compound 83
Molecular Weight:672.8053
Molecular Formula:C43H44O7
InChIKey:ZGMJOADIXTXWBY-UUMDEIPGSA-N
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Compound 84
Molecular Weight:428.5934
Molecular Formula:C24H32O5Si
InChIKey:LFFFMIFTNZMQNG-QPTUXGOLSA-N
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Compound 85
Molecular Weight:909.069
Molecular Formula:C56H60O11
InChIKey:CWQNXHWYDKYAKF-QFMGLQKWSA-N
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Compound 86
Molecular Weight:909.069
Molecular Formula:C56H60O11
InChIKey:CWQNXHWYDKYAKF-JFGSFINNSA-N
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Compound 87
Molecular Weight:179.1711
Molecular Formula:C6H13NO5
InChIKey:XVQRZUFFKHYAPA-SLPGGIOYSA-N
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Compound 89
Molecular Weight:240.2111
Molecular Formula:C7H16N2O7
InChIKey:QJOGYSMSJGSTQW-WYRLRVFGSA-N
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Compound 90
Molecular Weight:341.3117
Molecular Formula:C12H23NO10
InChIKey:LTZXPZQIBOHOPK-LIZSDCNHSA-N
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Compound 88
Molecular Weight:179.1711
Molecular Formula:C6H13NO5
InChIKey:WCWOEQFAYSXBRK-VFUOTHLCSA-N
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Compound 91
Molecular Weight:221.2078
Molecular Formula:C8H15NO6
InChIKey:IBONACLSSOLHFU-JAJWTYFOSA-N
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Compound 92
Molecular Weight:389.3545
Molecular Formula:C16H23NO10
InChIKey:CLOXUHNVVMZILR-IBEHDNSVSA-N
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Compound 93e
Molecular Weight:177.1983
Molecular Formula:C7H15NO4
InChIKey:AEFQSBOTZULPGP-ZTYPAOSTSA-N
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Compound 93b
Molecular Weight:273.95
Molecular Formula:C6H10Br2O2
InChIKey:YRHJHRDACDTZKW-ZELZYMQXSA-N
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Compound 93d
Molecular Weight:227.053
Molecular Formula:C6H11BrO4
InChIKey:ZPJWNLQKUBSNMY-UNTFVMJOSA-N
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Compound 93c
Molecular Weight:211.054
Molecular Formula:C6H11BrO3
InChIKey:YTMORFNIWVQAMT-ZELZYMQXSA-N
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Compound 93a
Molecular Weight:239.936
Molecular Formula:C6H8Br2
InChIKey:UPCQGURPQYFOKT-ZPUQHVIOSA-N
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Compound 94
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 95
Molecular Weight:340.2806
Molecular Formula:C12H20O11
InChIKey:CUKZGOBWGGOLIQ-QRDRGOPVSA-N
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Compound 96
Molecular Weight:232.2304
Molecular Formula:C10H16O6
InChIKey:YFXGITFCQCEEOU-IBZMGSLASA-N
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Compound 97
Molecular Weight:400.3772
Molecular Formula:C18H24O10
InChIKey:QJYZZUXNUBNGGV-UIRSAESWSA-N
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Compound 98
Molecular Weight:144.2114
Molecular Formula:C8H16O2
InChIKey:OXDOZKZGTKEASS-YUMQZZPRSA-N
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Compound 99
Molecular Weight:114.1424
Molecular Formula:C6H10O2
InChIKey:RYYFXSJXHNVZCA-YUDCMIJISA-N
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Compound 100
Molecular Weight:144.1684
Molecular Formula:C7H12O3
InChIKey:MZCKXSHPEXURLP-HKFDCFJWSA-N
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Compound 101
Molecular Weight:84.1164
Molecular Formula:C5H8O
InChIKey:ACZNIBVNGPLHAC-ONEGZZNKSA-N
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Compound 102
Molecular Weight:262.2564
Molecular Formula:C11H18O7
InChIKey:OBJUBBHXUIHXOD-VUZBNPQISA-N
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Compound 104
Molecular Weight:262.2564
Molecular Formula:C11H18O7
InChIKey:OBJUBBHXUIHXOD-RXUBDEDZSA-N
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Compound 103
Molecular Weight:102.1317
Molecular Formula:C5H10O2
InChIKey:XOHPJWXAFXEPJQ-YFKPBYRVSA-N
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Compound 105
Molecular Weight:102.1317
Molecular Formula:C5H10O2
InChIKey:XOHPJWXAFXEPJQ-RXMQYKEDSA-N
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