Stereoselective Synthesis of P‑Modified α‑Glycosyl Phosphates by the Oxazaphospholidine Approach

α-Glycosyl phosphate derivatives are widely known as constituents of biomolecules. To date, several types of non-natural α-glycosyl phosphates including “P-modified analogs” have been synthesized to investigate their characteristics. Herein a new approach to the stereoselective modification of the i...

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Bibliographic Details
Published in:Organic letters 2013-12, Vol.15 (23), p.5948-5951
Main Authors: Noro, Mihoko, Fujita, Shoichi, Wada, Takeshi
Format: Article
Language:English
Subjects:
Boron Compounds - chemistry
Glycocalyx - chemistry
Glycosides - chemical synthesis
Glycosides - chemistry
Leishmania - chemistry
Molecular Structure
Organophosphates - chemical synthesis
Organophosphates - chemistry
Polysaccharides - chemistry
Stereoisomerism
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Summary:α-Glycosyl phosphate derivatives are widely known as constituents of biomolecules. To date, several types of non-natural α-glycosyl phosphates including “P-modified analogs” have been synthesized to investigate their characteristics. Herein a new approach to the stereoselective modification of the intersugar phosphorus atom in α-glycosyl phosphates by use of the oxazaphospholidine method is presented. Via this approach, the dimers of α-glycosyl phosphorothioates and α-glycosyl boranophosphates were obtained efficiently and stereoselectively.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol402785h