The photochemistry of carbohydrate derivatives. Part 7. The synthesis of methyl 3,4-di-O-(β-D-glucopyranosyl)-α-L-rhamnopyranoside from photolabile methyl 2,3-O-(2-nitrobenzylidene)-α-L-rhamnopyranoside
- 1 January 1983
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 8,p. 1879-1884
- https://doi.org/10.1039/p19830001879
Abstract
Methyl endo/exo-2,3-O-(2-nitrobenzylidene)-α-L-rhamnopyranoside (1) was glucosylated to give the fully protected β-(1 → 4)-linked disaccharide derivative (5) as an endo/exo mixture which, upon photolysis and oxidation gave, after chromatography, the partially protected disaccharide (15) with an unprotected 3-hydroxy group. Further glucosylation at this position gave the fully blocked trisaccharide (17) which was de-esterified to give methyl 3,4-di-O-(β-D-glucopyranosyl)-α-L-rhamnopyranoside (18).This publication has 2 references indexed in Scilit:
- The photochemistry of carbohydrate derivatives. Part 6. Synthesis of 3-(methoxycarbonyl) propyl pyranosides of 2,3-di-O-(β-D-galactopyranosyl)-α-D-galactose and 3-O-(α-D-galactopyranosyl)-2-O-(β-D-galactopyranosyl)-α-D-galactose using photolabile O-(2-nitrobenzylidene) acetals as temporary blocking groupsJournal of the Chemical Society, Perkin Transactions 1, 1983
- The photochemistry of carbohydrate derivatives. Part 5. Synthesis of methyl 2,3-di-O-(β-D-glucopyranosyl)-α-L-fucopyranoside and methyl 2,3-di-O-(β-D-galactopyranosyl)-α-L-fucopyranoside using photolabile O-(2-nitrobenzylidene) acetals as temporary blocking groupsJournal of the Chemical Society, Perkin Transactions 1, 1983