We thank Prof. Kazuhiko Saigo (University of Tokyo) for helpful suggestions. This research was supported by grants from the Ministry of Education, Culture, Sports, Science, and Technology (MEXT) Japan and the Futaba Electronics Memorial Foundation (N.O.).
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Communication
Stereocontrolled Solid-Phase Synthesis of Oligonucleoside H-Phosphonates by an Oxazaphospholidine Approach†
Article first published online: 4 NOV 2008
DOI: 10.1002/anie.200804408
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Iwamoto, N., Oka, N., Sato, T. and Wada, T. (2009), Stereocontrolled Solid-Phase Synthesis of Oligonucleoside H-Phosphonates by an Oxazaphospholidine Approach. Angew. Chem. Int. Ed., 48: 496–499. doi: 10.1002/anie.200804408
- †
Publication History
- Issue published online: 29 DEC 2008
- Article first published online: 4 NOV 2008
- Manuscript Received: 6 SEP 2008
Funded by
- Ministry of Education, Culture, Sports, Science, and Technology (MEXT) Japan
- Futaba Electronics Memorial Foundation
Keywords:
- asymmetric synthesis;
- H-phosphonates;
- oligonucleotides;
- solid-phase synthesis
Stereodefined oligonucleosideH-phosphonates were synthesized on a solid support using diastereopure nucleoside 3′-O-oxazaphospholidine monomers. Several stereodefined backbone-modified analogues were obtained with the oligonucleoside H-phosphonates as precursors (see scheme; BPRO=protected nucleobase, DMTr=4,4′-dimethoxytrityl, Th=thymin-1-yl, TfO−=triflate).