Fluorination reactions at C-4 of methyl 2-O-benzyl-3,6-dideoxyhexopyranosides with diethylaminosulfur trifluoride (DAST) and with tris(dimethylamino)sulfonium difluorotrimethylsilicate (TASF)

DOI: 10.1248/cpb.39.1088

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 1088 - 1090 (1991)

Update date:2022-07-29

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Authors:

Mori Mori

Morishima

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Article abstract of DOI:10.1248/cpb.39.1088

Fluorination at C-4 of methyl 2-O-benzyl-3,6-dideoxy-α-D-ribo- and α-D-arabino-hexopyranosides (1 and 5) using diethylaminosulfur trifluoride (DAST) proceeded with exclusive retention of configuration. But treating the triflates of 1 and 5 with tris(dimethylamino)sulfonium difluorotrimethylsilicate (TASF) afforded mostly the configurationally inverted fluorides.

Full text of DOI:10.1248/cpb.39.1088

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