✦ LIBER ✦

Synthesis and characterization of propyl O-β-d-galactopyranosyl-(1→4)-O-β-d-galactopyranosyl-(1→4)-α-d-galactopyranoside

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

Publisher: Elsevier Science
Year: 1984
Tongue: English
Weight: 571 KB
Volume: 131
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(84)85245-3

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✦ Synopsis

Ally1 4-0-(4-O-acetyl-2-O-benzoyl-3,6-di-O-benzyl-~-D-galactopyranosyl)-2-0-benzoyl-3,6-di-O-benzyl-a-D-galactopyranoside was 0-deallylated to give the 1-hydroxy derivative, and this was converted into the corresponding l-O-(Nphenylcarbamoyl) derivative, treatment of which with dry HCl produced the a-Dgalactopyranosyl chloride. This was converted into the corresponding 2,2,2-trifluoroethanesulfonate, which was coupled to ally1 2-O-benzoyl-3,6-di-O-benzyl-a-D-galactopyranoside, to give crystalline ally1 4-O-[4-O-(4-O-acetyl-2-O-benzoyl-3,6-di-O-benzyl-~-D-galactopyranosyl)-2-O-~nzoyl-3,6-di-O-benzyl-~-D-galactopyranosyl]-2-O-benzoyl-3,6-di-O-benzyl-a-D-galactopyranoside (15) in 8.5% yield, no trace of the LY anomer being found. The trisaccharide derivative 15 was de-esterified with 2% KCN in 95% ethanol, and the product 0-debenzylated with HZ Pd, to give the unprotected trisaccharide. Alternative sequences are discussed.

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