The allyl ether as a protecting group in carbohydrate chemistry. Part VII. The 2-O-allyl group as a non-participant in 1,2-cis-glycoside synthesis
- 1 January 1975
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 4,p. 361-363
- https://doi.org/10.1039/p19750000361
Abstract
2-O-Allyl-3,4,6-tri-O-benzyl-D-galactopyranose was prepared and converted into the corresponding galactosyl chloride. The chloride was condensed with benzyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside to give crystalline benzyl 6-O-(2-O-allyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl)-2,3,4-tri-O-benzyl-α-D-galactopyranoside. The allyl group was removed from this fully protected disaccharide to give a disaccharide derivative suitable for conversion into a trisaccharide or for oxidation to a ketone and subsequent conversion into a disaccharide containing an α-linked 2-amino-2-deoxy-sugar.Keywords
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