A new synthesis of 4- O-α- d-galactopyranosyl- d-galactopyranose

The bromide-catalyzed condensation of 2,3,4,6-tetra- O-benzyl- d-galactopyranosyl bromide ( 11) with methyl 2,3,6-tri- O-benzoyl-α- d-galactopyranoside ( 3) gave methyl 2,3,6-tri- O-benzoyl-4- O-(2,3,4,6-tetra- O-benzyl-α- d-galactopyranosyl)-α- d-galactopyranoside ( 12) in 83% yield. The yield of t...

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Bibliographic Details
Published in:Carbohydrate research 1978, Vol.62 (2), p.245-252
Main Authors: Cox, Daniel D., Metzner, E.Kurt, Reist, Elmer J.
Format: Article
Language:English
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Summary:The bromide-catalyzed condensation of 2,3,4,6-tetra- O-benzyl- d-galactopyranosyl bromide ( 11) with methyl 2,3,6-tri- O-benzoyl-α- d-galactopyranoside ( 3) gave methyl 2,3,6-tri- O-benzoyl-4- O-(2,3,4,6-tetra- O-benzyl-α- d-galactopyranosyl)-α- d-galactopyranoside ( 12) in 83% yield. The yield of this glycosidation reaction was high, despite the axial orientation of the 4-hydroxyl group of 3. Stepwise deprotection of 12 afforded methyl 4- O-α- d-galactopyranosyl-α- d-galactopyranoside ( 15). Acetylation of 15, followed by acetolysis, gave the known α-octaacetate 17. This scheme constituted a total synthesis of 4- O-α- d-galactopyranosyl- d-galactopyranose ( 2) in 25% yield from 3. The disaccharide 2 is the terminal disaccharide of the ceramide trisaccharide related to Fabry's disease.
ISSN:0008-6215
1873-426X
DOI:10.1016/S0008-6215(00)80871-X