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A new method of oligosaccharide synthesis: Rhamnotrioses

✍ Scribed by Alina Jaworska; Aleksander Zamojski

Publisher
Elsevier Science
Year
1984
Tongue
English
Weight
563 KB
Volume
126
Category
Article
ISSN
0008-6215

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✦ Synopsis

Condensation

of partially protected rhamnobiose derivatives with l-Oacetyl-2,3,6-trideoxy-cY,P-DL-glycero-hex-2-enopyranos-4-ulose afforded pairs of diastereoisomeric a-linked trisaccharide derivatives to which the configuration was assigned on the basis of spectral and chemical data. Reduction of the carbonyl group in these products led to 2",3"-unsaturated trisaccharide derivatives containing a 2,3_unsaturated cy-erythro unit. cis-Hydroxylation of the double bond in five of these unsaturated compounds gave rhamnotriose derivatives, two of which were deprotected to give the trisaccharides a-L-Rhap-( 1+2)-cY-L-Rhap-( 1+3)-L-Rhap and cY-D-Rhap-( 1+2)-a-L-Rhap-( 1+3)-L-Rhap, respectively.

πŸ“œ SIMILAR VOLUMES

A new method of oligosaccharide synthesi
A new method of oligosaccharide synthesis: Rhamnobioses
✍ Alina Jaworska; Aleksander Zamojski πŸ“‚ Article πŸ“… 1984 πŸ› Elsevier Science 🌐 English βš– 844 KB

A semi-synthetic approach to (1+2)-(r-and (l-3)-a-linked rhamnobioses is presented. The method involves condensation of benzyl2-O-or 3-0-benzoyl-4-0benzyl-a-L-rhamnopyranoside (5) with l-O-acetyl-2,3,6-trideoxy-a,P-DL-glycerohex-2-enopyranos-4-ulose (6)) isolation of the L-L and D-L forms of the res