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Studies on the synthesis of propyl 4-O-β-d-galactopyranosyl-α-d-galactopyranoside

✍ Scribed by Hamdy A. El-Shenawy; Conrad Schuerch

Publisher
Elsevier Science
Year
1984
Tongue
English
Weight
930 KB
Volume
131
Category
Article
ISSN
0008-6215

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✦ Synopsis

2-O-Benzoyl-3,6-di-O-benzyl-4-0-(chloroacetyl)-, 4-O-acetyl-ZO-benzoyl-3,6-di-0-benzyl-, and 2-O-benzoyl-3,4,6-tri-O-benzyl-cY-D-galactopyranosyl chloride were converted into the corresponding 2,2,2-trifluoroethanesulfonates, and these were treated with ally1 2-0-benzoyl3,6-di-O-benzyl-cw-D-galactopyranoside, to give ally1 2-0-benzoy1-4-0-[2-0-benzoy1-3,6-di-0-benzy1-4-0-(chloroacetyl)-~-D-galactopyranosy1]-3,6-di-O-benzyl-cY-D-galactopyranoside (26; 41% yield), ally1 4-0-(4-0-acetyl-2-0-benzoyl-3,6-di-O-benzyl-~-D-galactopyranosyl)-2-O-benzoyl-3,6-di-O-benzyl-cY-D-galactopyranoside (27; 62% yield), and ally1 2-O-benzoyl-4-0-(2-O-benzoyl-3,4,6-tri-O-benzyl-~-D-galactopyranosyl)-3,6-di-0-benzyl-Lu-D-galactopyranoside (28; 65% yield). All disaccharides were free from their (Y anomers. Disaccharides 26 and 27 were found to be base-sensitive, and were de-esterified by KCN in aqueous ethanol, and debenzylated with HTPd. Attempts to produce (l-+4)-/3-D-galactopyranosides from the coupling of a number of fully esterified D-galactopyranosyl sulfonates to ally1 2,3,6-tri-o-benzoyl-cY-D-galactopyranoside were unsuccessful.

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