Synthesis of blood-group substances. Part 8. A synthesis of the branched trisaccharide 2-acetamido-2-deoxy-4-O-(α-L-fucopyranosyl)-3-O-(β-D-galactopyranosyl)-D-glucopyranose
- 1 January 1979
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 2,p. 319-322
- https://doi.org/10.1039/p19790000319
Abstract
Reaction of 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide with benzyl 2-acetamido-4-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside provided crystalline benzyl 2-acetamido-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-4-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside in 87% yield. Deallylation followed by condensation with 1-O-(N-methyl) acetimidyl-2,3,4-tri-O-benzyl-β-L-fucopyranose provided the crystalline derivative (13). The title trisaccharide was obtained after O-deacetylation followed by catalytic hydrogenolysis. Preparations of 2-acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-D-glucopyranose and 2-acetamido-2-deoxy-4-O-(α-L-fucopyranosyl)-D-glucopyranose are reported.Keywords
This publication has 2 references indexed in Scilit:
- Synthesis of blood-group substances. Part 7. Synthesis of the branched trisaccharide O-α-L-fucopyranosyl-(1 → 3)-[O-β-D-galactopyranosyl-(1 → 4)]-2-acetamido-2-deoxy-D-glucopyranoseJournal of the Chemical Society, Perkin Transactions 1, 1979
- Synthesis of blood-group substances. 6. Synthesis of O-.alpha.-L-fucopyranosyl-(1 .fwdarw. 2)-O-.beta.-D-galactopyranosyl-(1 .fwdarw. 4)-O-[.alpha.-L-fucopyranosyl-(1 .fwdarw. 3)]-2-acetamido-2-deoxy-.alpha.-D-glucopyranose, the postulated Lewis d antigenic determinantThe Journal of Organic Chemistry, 1977