The synthesis of methyl 4-O-(4-O-α-d-galactopyranosyl-β-d-galactopyranosyl)-β-d-glucopyranoside: The methyl β-glycoside of the trisaccharide related to Fabry's disease

Add time:08/31/2019    Source:sciencedirect.com

As part of a program to synthesize the ceramide trisaccharide (1) related to Fabry's disease, methyl 4-O-(4-O-α-d-galactopyranosyl-β-d-galactopyranosyl)-β-d-glucopyranoside (12) was prepared. Methyl β-lactoside (2) was converted into methyl 4-O-(4,6-O-benzylidene-β-d-galactopyranosyl)-β-d-glucopyranoside (4). Methyl 2,3,6-tri-O-benzoyl-4-O-(2,3,6-tri-O-benzoyl-β-d-galactopyranosyl)-β-d-glucopyranoside (7) was synthesized from 4 through the intermediates methyl 2,3,6-tri-O-benzoyl-4-O-(4,6-O-benzylidene-2,3-di-O-benzoyl-β-d-galactopyranosyl)-β-d-glucopyranoside (5) and methyl 2,3,6-tri-O-benzoyl-4-O-(2,3-di-O-benzoyl-β-d-galactopyranosyl)-β-d-glucopyranoside (6). The halide-catalyzed condensation of 7 with 2,3,4,6-tetra-O-benzyl-d-galactopyranosyl bromide (8) gave methyl 2,3,6-tri-O-benzoyl-4-O-[2,3,6-tri-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzyl-α-d-galactopyranosyl)- β-d-galactopyranosyl]-β-d-glucopyranoside (10). Stepwise deprotection of 10 led to 12, the methyl β-glycoside of the trisaccharide related to Fabry's disease.

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