Journal of Carbohydrate Chemistry

Modification at c-6 of unprotected glucopyranosyl fluoride using 6-Bromo-6-deoxy-α-d-glucopyranosyl Fluoride as the key compound.

AM Horneman, I Lundt

Index: Horneman, Anne Marie; Lundt, Inge Journal of Carbohydrate Chemistry, 1995 , vol. 14, # 1 p. 1 - 8

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Citation Number: 4

Abstract

Abstract 6-Bromo-6-deoxy-α-d-glucopyranosyl fluoride (2) was prepared in good yield from α-d-glucopyranosyl fluoride (1) by treatment with PPh3 and CBr4 in pyridine. Catalytic reduction of 2 gave the corresponding 6-deoxy-α-d-glucopyranosyl fluoride (3) while treatment with NaN3 in DMF gave the 6-azido-6-deoxy-α-d-glucopyranosyl fluoride (4). The latter could be reduced to the 6-amino-6-deoxyglucosyl fluoride (5) which was converted ...