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Large-scale synthesis of β-l-fucopyranosyl phosphate and the preparation of GDP-β-l-fucose

✍ Scribed by Kim Adelhorst; George M. Whitesides

Publisher: Elsevier Science
Year: 1993
Tongue: English
Weight: 620 KB
Volume: 242
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(93)80022-7

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✦ Synopsis

A practical 15-mmol large-scale synthesis of beta-L-fucopyranosyl dicyclohexylammonium phosphate from L-fucose in 63% overall yield was developed. The synthesis took advantage of a neighboring Bz-2 group participating in a Koenigs-Knorr-like glycosylation. The sugar phosphate was transformed into the activated sugar nucleoside, guanosine diphosphate beta-L-fucopyranose, on a gram scale.

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