Single‐Step Multisyntheses of Glycosyl Acceptors: Benzylation of n‐1 Hydroxyl Groups of Phenylthio Glycosides of Xylose, Mannose, Glucose, Galactose, 2‐Azido‐2‐deoxy‐glucose, and 2‐Azido‐2‐deoxy‐galactose

Abstract

An array of synthons is required to access an oligosaccharide library; however, multistep and thus time‐consuming synthesis is inevitable. To rapidly access such synthetic units, multiple benzylation reactions of monosaccharides under phase‐transfer conditions were examined. Multiple benzyl groups were successfully incorporated in one step, especially in the cases of reactions with triol systems.

Keywords:

• Phase transfer
• Benzylation
• Random reactions
• Thioglycosides
• Glycosyl acceptors

Acknowledgments

We thank Dr. Y. Kanie for her critical disscussions on separation of a series of product mixture by HPLC. This work was supported in part by Key Technology Research Promotion Program, The New Energy and Industrial Development Organization (NEDO), Ministry of Economy, Trade and Industry (METI) of Japan.