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Dibromination of benzyloxy-groups: Glycosyl bromides from benzyl glycosides

โœ Scribed by P.M. Collins; P. Premaratne; A. Manro; A. Hussain

Book ID
104233226
Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
133 KB
Volume
30
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Brominafion of benzyloxy groups in sugar derivatives

with bromotrichloromethane and ultraviolet light rapidly gives a-bromobenzyloxy sugars. On further irradiation a, a-dibromobenzyloxy derivatives are formed from benzyl sugar ethers, whereas glycosyl bromides are produced from benzyl furanosides and pyranosides.

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A convenient one-pot preparation of glyc
A convenient one-pot preparation of glycosyl bromides as well as glycosyl acetates from benzyl glycosides using N-bromosuccinimide.
โœ Hironobu Hashimoto; Manabu Kawa; Yoshihiro Saito; Tomoko Date; Shigeomi Horito; ๐Ÿ“‚ Article ๐Ÿ“… 1987 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 230 KB

Some conversions of benzyl glycoside using NBS were examined and one-pot preparation of glycosyl acetates and bromides were developed. An efficient 0-debenzylation at non-anomeric position was also observed.