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Stereoselective synthesis of C-glycosides via Tebbe methylenation and Claisen rearrangement

✍ Scribed by H.Yasmin Godage; Antony J Fairbanks

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
141 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis

A variety of b-C-glycosides may be readily accessed in a stereoselective fashion from 3-OH glycal esters, via the use of Tebbe methylenation and subsequent thermal Claisen rearrangement. The use of carbohydrate ester substrates allows the formation of b( 16) linked C-disaccharides.

πŸ“œ SIMILAR VOLUMES

Synthesis of Ξ±-C-glycosides via tandem T
Synthesis of Ξ±-C-glycosides via tandem Tebbe methylenation and Claisen rearrangement
✍ H.Yasmin Godage; Antony J. Fairbanks πŸ“‚ Article πŸ“… 2003 πŸ› Elsevier Science 🌐 French βš– 264 KB

A variety of a-C-glycosides may be accessed in an entirely stereoselective fashion from 3-OH glycal esters, by way of the tandem reaction sequence of Tebbe methylenation and Claisen rearrangement. In contrast with previous studies in the corresponding b-series, careful control of conditions for Clai