Crystal and molecular structures of benzyl 3-O-benzoyl-4-O-benzyl-2-O-(2,3,6-trideoxy-α-l-glycero-hex-2-enopyranosyl-4- ulose)-α-l-rhamnopyranoside
✍ Scribed by Janusz W. Krajewski; Zofia Urbańczyk-Lipkowska; Przemyslaw Gluziński; Aleksander Zamojski; Katarzyna Stadnicka
- Publisher
- Elsevier Science
- Year
- 1983
- Tongue
- English
- Weight
- 559 KB
- Volume
- 117
- Category
- Article
- ISSN
- 0008-6215
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Condensation of 2,4-di-O-acetyl-3,6-di-O-methyl-a-~glucopyranosyl bromide with either ally1 or benxyl2,4-di-0-methyl-cu+rhamnopyranoside in the presence of mercuric cyanide, followed by 0-deacetylation, gave the title oligosaccharides in excellent yields.
Syntheses of the title glycosides are described. The critical O-glycosylations were carried out in the presence of boron trifluoride etherate with a high degree of alpha-selectivity.
Acylated ]3-o-xylopyranose derivatives are known to exist as a mixture of the 1C 4 and 4C I conformers in rapid equilibrium in solution [3]. Several conformations have also been reported for/3-D-xylopyranose derivatives in the solid state [4]. In the course of our study to investigate the functions
The title branched-trisaccharide derivatives (9 and 13) have been synthesised from methyl 2,3-O-(2-nitrobenzylidene)-a-L-rhamnopyranoside (2) using the 2nitrobenzylidene residue as a temporary blocking-group. Condensation of 2 with methyl (2,3,4-tri-O-acetyl-a-D-glucopyranosyl bromide)uronate afford