Selektive Phosphorylierung von Nucleosiden
Abstract
Phosphorsäure‐bis‐[β.β.β‐trichlor‐äthylester]‐chlorid eignet sich zur selektiven Phosphorylierung von Nucleosiden in 5′‐Stellung. Die entstehenden Nucleosid‐5′‐bis‐[β.β.β‐trichloräthyl]‐phosphate lassen sich in Ausbeuten von 40–70% isolieren. Die Triester werden durch Behandeln mit Zinkstaub in Nucleosid‐5′‐phosphate übergeführt.
Number of times cited: 26
- Tse‐Lok Ho, Mary Fieser and Louis Fieser, Bis(2,2,2‐Trichloroethyl) Phosphorochloridate, Fieser and Fieser's Reagents for Organic Synthesis, (2006).
- Toshiaki Matsui, Takashi Kondo, Yoshitaka Nishita, Satoshi Itadani, Hiroshi Tsuruta, Setsuko Fujita, Nagashige Omawari, Masaru Sakai, Shuichi Nakazawa, Akihito Ogata, Hideaki Mori, Wataru Kamoshima, Kouichiro Terai, Hiroyuki Ohno, Takaaki Obata, Hisao Nakai and Masaaki Toda, Highly potent inhibitors of tnf-α production. Part II: metabolic stabilization of a newly found chemical lead and conformational analysis of an active diastereoisomer, Bioorganic & Medicinal Chemistry, 10, 12, (3787), (2002).
- Paul Knochel, Paul Knochel, Nathalie Grenouillat and Vikas Sikervar, Zinc, Encyclopedia of Reagents for Organic Synthesis, (1-18), (2017).
- Paul Knochel, Paul Knochel and Nathalie Grenouillat, Zinc, Encyclopedia of Reagents for Organic Synthesis, (2006).
- Paul Knochel, Zinc, Encyclopedia of Reagents for Organic Synthesis, (2001).
- Isabel Mathieu‐Pelta and Slayton A. Evans, Bis(2,2,2‐trichloroethyl) Phosphorochloridate, Encyclopedia of Reagents for Organic Synthesis, (2001).
- Trupti Desai, Alfonso Fernandez-Mayoralas, Jill Gigg, Roy Gigg and Sheila Payne, The preparation of phosphorylated intermediates for the synthesis of racemic and chiral myo-inositol 1,4,5-trisphosphate and its phosphorothioate analogues, Carbohydrate Research, 234, (157), (1992).
- C. McGuigan, T. J. O'Connor, S. R. Nicholls, C. Nickson and D. Kinchington, Synthesis and anti-HIV Activity of Some Novel Substituted Dialkyl Phosphate Derivatives of AZT and ddCyd, Antiviral Chemistry and Chemotherapy, 1, 6, (355), (1990).
- David C. Palmer, Jerauld S. Skotnicki and Edward C. Taylor, 3 Synthesis of Analogues of Folic Acid, Aminopterin and Methotrexate as Antitumour Agents, , 10.1016/S0079-6468(08)70278-9, (85-231), (1988).
- Thomas Ciardelli, Charles J. Stewart, Annemarie Seeliger and Theodor Wieland, Synthesis of a carba‐analog of S‐palmitoyl‐coenzyme A, heptadecan‐2‐onyldethio‐CoA, and of S‐Heptadecyl‐CoA; effective inhibitors of citrate synthase and carnitine palmitoyltransferase, Liebigs Annalen der Chemie, 1981, 5, (828-841), (2006).
- Peter Kohler, Michael Wachtl and Christoph Tamm, , Helvetica Chimica Acta, 63, 8, (2488-2494), (2004).
- Morio Ikehara, Eiko Ohtsuka and Alexander F. Markham, The Synthesis of Polynucleotides, Advances in Carbohydrate Chemistry and Biochemistry Volume 36, 10.1016/S0065-2318(08)60236-X, (135-213), (1979).
- Fausto Ramirez and James F. Marecek, Phosphorylation by means of cyclic enediol phosphates, Accounts of Chemical Research, 10.1021/ar50126a003, 11, 6, (239-245), (2002).
- Felix Waldmeier and Christoph Tamm, , Helvetica Chimica Acta, 61, 5, (1648-1663), (2004).
- Hiroshi Takaku, Toshimi Konishi and Tsujiaki Hata, 8-QUINOLYL NUCLEOSIDE 5′-PHOSPHATES AS A USEFUL INTERMEDIATE FOR THE SYNTHESIS OF NUCLEOSIDE 5′-DI- AND 5′-TRI-PHOSPHATES, Chemistry Letters, 6, 6, (655), (1977).
- Alan H. Haines, Relative Reactivities of Hydroxyl Groups in Carbohydrates, Advances in Carbohydrate Chemistry and Biochemistry Volume 33, 10.1016/S0065-2318(08)60280-2, (11-109), (1976).
- Julien P. H. Verheyden, Ian D. Jenkins, Geoffrey R. Owen, Slobodan D. Dimitrijevich, Colin M. Richards, Prem C. Srivastava, Nghiep Le‐Hong and John G. Moffatt, SYNTHESIS OF CERTAIN 4′‐SUBSTITUTED NUCLEOSIDES, Annals of the New York Academy of Sciences, 255, 1, (151-165), (2006).
- Tsujiaki Hata, Isamu Yamamoto and Mitsuo Sekine, A SIMPLE METHOD FOR THE SYNTHESIS OF 5′-AZIDO-5′-DEOXYRIBONUCLEOSIDES, Chemistry Letters, 4, 9, (977), (1975).
- Yoshihiko Taguchi and Yoshitaka Mushika, 2-(N,N-dimethylamino)-4-nitrophenyl phosphate and its use in the selective phosphorylation of unprotected nucleoside., Tetrahedron Letters, 16, 24, (1913), (1975).
- Hiroshi Takaku and Yoshifusa Shimada, Studies of phosphorylation. IV A selective phosphorylation of 5′-hydroxy group of nugleosides by means of tirs(8-quinolyl) phosphate, Tetrahedron Letters, 15, 14, (1279), (1974).
- Thomas I. Kalman, Alexander Bloch, Gabor L. Szekeres and Thomas J. Bardos, Methylation of 4-thio-2′-deoxyuridylate by thymidylate synthetase, Biochemical and Biophysical Research Communications, 55, 1, (210), (1973).
- U. Séquin and Ch. Tamm, Nucleosides and Nucleotides. Part 2: Synthesis of both anomers of 1‐(5′‐O‐phosphoryl‐2′‐deoxy‐D‐ribofuranosyl)‐2(1H)‐pyridone [1], Helvetica Chimica Acta, 55, 4, (1196-1218), (2004).
- Thomas J. Bardos, Chapter 31. Nucleosides and Nucleotides, , 10.1016/S0065-7743(08)60354-1, (333-345), (1970).
- Bernd Jastorff and Hans Hettler, Nucleotid‐Analoge von 5′‐Amino‐5′‐desoxy‐nucleosiden, Chemische Berichte, 102, 12, (4119-4127), (2006).
- Friedrich Cramer, Modified nucleotides as tools in nucleic acid research, Accounts of Chemical Research, 2, 11, (338), (1969).
- B. Jastorff and H. Hettler, Phosphorylation of 5′-amino-5′-deoxynucleosides, Tetrahedron Letters, 10, 30, (2543), (1969).




