The photochemistry of carbohydrate derivatives. Part 5. Synthesis of methyl 2,3-di-O-(?-D-glucopyranosyl)-?-L-fucopyranoside and methyl 2,3-di-O-(?-D-galactopyranosyl)-?-L-fucopyranoside using photolabile O-(2-nitrobenzylidene) acetals as temporary blocking groups
✍ Scribed by Collins, Peter M.; Munasinghe, V. Ranjit N.
- Book ID
- 119998775
- Publisher
- Royal Society of Chemistry
- Year
- 1983
- Weight
- 893 KB
- Volume
- 0
- Category
- Article
- ISSN
- 1472-7781
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📜 SIMILAR VOLUMES
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
Treatment of benzyl O-/?-n-galactopyranosyl-( 1+3)-2-acetamido-2-deoxy-4,6-O-isopropylidene-j3-D-glucopyranoside with tert-butylchlorodiphenylsiiane afforded the 6'-0-tert-butyldiphenylsilyl ether, which was converted into the 3',4'-0-isopropylidene derivative. Methylation and subsequent removal of
Allyl 4-O-benzyl-~-L-rhamnopyranoside was converted into allyl 4-O-benzyl-3-O-methyl-oeL-rhamnopyranoside and this was condensed with 2,3,4-tri-O-acetyl-~-L-rhamnopyranosyl chloride to give a disaccharide derivative which was converted into allyl 4 This disaccharide derivative was condensed with 2,