Organoboron monosaccharides, XVIII. Stereoselective syntheses of β-D-lyxofuranosyl glycosides
✍ Scribed by Dahlhoff, Wilhelm V.
- Publisher
- John Wiley and Sons
- Year
- 1990
- Tongue
- English
- Weight
- 341 KB
- Volume
- 1990
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
Abstract
Methyl and phenyl β‐D‐lyxofuranoside (3a and 3b) are prepared by reaction of 5‐O‐acetyl‐2,3‐O‐ethylboranediyl‐α‐D‐lyxofuranosyl bromide (1) with sodium methoxide and sodium phenoxide to give the protected glycosides 2a, b followed by deboronation and deacetylation. The protected α‐D‐lyxofuranosyl disaccharides 2c, d are synthesized by treatment of 1 with 1,2:3,4‐di‐O‐isopropylidene‐α‐D‐galactopyranose and 1,2:5,6‐di‐O‐isopropylidene‐α‐D‐glucofuranose after the former has been converted to its sodium organooxytriethylborate and the latter has been O‐tributylstannylated. 2c and 2d are deboronated and deacetylated to give 3c and 3d, respectively. 2,3,5‐Tri‐O‐acetyl‐β‐D‐lyxofuranosyl glycosides (4a–d) are obtained from 3a–d by acetylation.