Stereoselective synthesis of P-modified α-glycosyl phosphates by the oxazaphospholidine approach.

Org Lett

Department of Medical Genome Sciences, Graduate School of Frontier Sciences, The University of Tokyo , Bioscience Building 702, 5-1-5 Kashiwanoha, Kashiwa, Chiba 277-8562, Japan, and Department of Medicinal and Life Schience, Faculty of Pharmaceutical Sciences, Tokyo University of Science 2641, Yamazaki, Noda, Chiba 278-8510, Japan.

Published: December 2013

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.

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http://dx.doi.org/10.1021/ol402785hDOI Listing

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