Bulletin of the Chemical Society of Japan

Fluorination Reactions at C-5 of 3-O-Benzyl-6-deoxy-1, 2-O-isopropylidenehexofuranoses.

Y Mori, N Morishima

Index: Mori, Yoko; Morishima, Naohiko Bulletin of the Chemical Society of Japan, 1994 , vol. 67, # 1 p. 236 - 241

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Citation Number: 13

Abstract

Fluorination reactions of 2-O-benzyl-6-deoxy-1, 2-O-isopropylidene-α-D-gluco-, β-L-ido-, α- D-allo-, and β-L-talo-furanoses (1, 2, 3, and 4) were investigated. The reaction of 1 with diethylaminosulfur trifluoride (DAST) predominantly produced 2-O-benzyl-5, 6-dideoxy-5- fluoro-1, 2-O-isopropylidene-α-D-glucofuranose with the retention of the configuration at C- 5. Both of the fluorides with retained and inverted configurations were obtained in the ...

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