Carbohydrate research

Synthesis of 4-deoxy and 4-deoxy-4-halogeno derivatives of l-fucose as potential enzyme inhibitors

TK Lindhorst, J Thiem

Index: Lindhorst, Thisbe K.; Thiem, Joachim Carbohydrate Research, 1991 ,  vol. 209, p. 119 - 129

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Citation Number: 22

Abstract

Abstract Methyl 2, 3-di-O-benzoyl-6-deoxy-α-l-galactopyranoside (2) was converted into the 4-deoxy-4-iodo-α-l-gluco derivative 4 by triflate-mediated inversion. Catalytic reduction of 4 gave methyl 2, 3-di-O-benzoyl-4, 6-dideoxy-α-l-xylo-hexopyranoside (6) and subsequent O- debenzoylation gave methyl 4, 6-dideoxy-α-l-xylo-hexopyranoside (7). Selective benzoylation of l-fucose gave 1, 2, 3-tri-O-benzoyl-α-l-fucopyranose (14). An analogous ...