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Synthesis of 3′- and 4′-deoxyfluorolactose and its Me3SiCH2CH2 and ceramide derivatives

✍ Scribed by Tomas Ekberg; Göran Magnusson

Publisher: Elsevier Science
Year: 1993
Tongue: English
Weight: 739 KB
Volume: 249
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(93)84065-e

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✦ Synopsis

(2-Trimethylsilyl)ethyl (Me3SiCH2CH2)3'- and 4'-deoxyfluorolactosides (1 and 3) were synthesized by glycosylation of Me3SiCH2CH2 2,3,6-tri-O-benzyl-beta-D-glucopyranoside with 2,4,6-tri-O-acetyl-3-deoxy-3-fluoro-beta-D-galactopyranosyl bromide and 2,3,6-tri-O-benzyl-4-deoxy-4-fluoro-beta-D-galactopyranosyl bromide. Anomeric deblocking of the fully acetyled Me3SiCH2CH2 glycosides (12 and 13) gave the corresponding hemiacetals 14 and 15. Removal of the acetyl groups gave 3'- and 4'-deoxyfluorolactose (2 and 4). The deoxyfluorolactosylceramides 5 and 6 were synthesized via boron trifluoride etherate- or silver triflate-activation of the trichloroacetimidates prepared from 14 and 15. Silver triflate-mediated glycosylations showed lower reaction rates, and fewer byproducts were formed.

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