The Journal of Organic Chemistry

Fluorinated carbohydrates. 2. Selective fluorination of gluco-and mannopyranosides. Use of 2-D NMR for structural assignments

PJ Card, GS Reddy

Index: Card, Peter J.; Reddy, Gade S. Journal of Organic Chemistry, 1983 , vol. 48, # 24 p. 4734 - 4743

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Citation Number: 67

Abstract

Methyl and phenyl a-glucosides, or suitably protected derivatives, may be selectively fluorinated with (diethy1amino) sulfur trifluoride (DAST) at the 4-or 6-position to afford the corresponding fluorinated galacto-or glucopyranoside. In contrast to the a-glucosides, the@- glucosides underwent ring fluorination at C-3 to give the 3-deoxy-3-fluoro-@-allo derivatives. High yields of primary fluorinated (C-6) products were obtained from both a- ...