Facile Preparation of 1, 6-Anhydro-2-azido-3-O-benzyl-2-deoxy-. BETA.-D-glucopyranose and Its 4-O-Substituted Derivatives.

…, S Takahashi, F Wang, Y Ueno, H Kuzuhara

Index: Sakairi, Nobuo; Takahashi, Shunya; Wang, Feng; Ueno, Yoshihito; Kuzuhara, Hiroyoshi Bulletin of the Chemical Society of Japan, 1994 , vol. 67, # 6 p. 1756 - 1758

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Citation Number: 12

Abstract

Treatment of 1, 6-anhydro-2, 3-O-endo-benzylidene-β-D-mannopyranose derivatives with trimethylamine–borane (1/1)–aluminium chloride resulted in highly regioselective fission of the cyclic acetals to give the corresponding 2-O-unprotected-3-O-benzyl derivatives. Trifluoromethanesulfonylation of these, followed by nucleophilic substitution, afforded 2- azido-2-deoxy derivatives in good yields.