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 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.
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.
Mihoko
M
Noro
Shoichi
S
Fujita
Takeshi
T
Wada
D001896:Boron Compounds / Q000737:chemistry; D019276:Glycocalyx / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D007891:Leishmania / Q000737:chemistry; D015394:Molecular Structure; D010755:Organophosphates / Q000138:chemical synthesis* / Q000737:chemistry; D011134:Polysaccharides / Q000737:chemistry; D013237:Stereoisomerism
D001896:Boron Compounds; D006027:Glycosides; D010755:Organophosphates; D011134:Polysaccharides