Journal of the Chemical Society. Perkin transactions I p. 1626 - 1629 (1981)
Update date:2022-08-02
Topics:
Veyrieres, Alain
Condensation of benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (2) with 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide, followed by de-O-acetylation, acetonation, O-benzoylation, and acidic hydrolysis afforded the 3',4'-diol (5) derived from N-acetyl-lactosamine.This compound was selectively glycosylated at the 3'-position by the oxazoline (7) derived from lactosamine to give the protected tetrasaccharide (8) in 52percent yield.Removal of the protecting groups gave the free tetrasaccharide β-D-Galp-(1->4)-β-D-GlcpNAc-(1->3)-β-D-Galp-(1->4)-D-GlcpNAc (9), a β-(1->3) dimer of N-acetyl-lactosamine.This structure has been found in various glycolipids isolated from erythrocyte membranes and could be recognized by several anti-i antisera.
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Doi:10.1021/ja0466659
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(1981)
