Carbohydrate Research p. 33 - 42 (1982)
Update date:2022-08-05
Topics:
Szurmai, Zoltan
Liptak, Andras
Benzyl 2-O-acetyl-4,6-O-benzylidene-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-β-D-galactopyranoside (11) has been synthesised by two routes.Partial deacetylation of 11 and then acid hydrolysis yielded benzyl 2-O-acetyl-3-O-α-L-rhamnopyranosyl-β-D-galactopyranoside, catalytic hydrogenolysis of which gave the first title compound in excellent yield.Benzyl 4,6-O-benzylidene-3-O-α-L-rhamnopyranosyl-β-D-galactopyranoside was benzylated, and hydrogenolysis (LiAlH4-AlCl3) of the product gave the disaccharide derivative 16 with only HO-6 unsubstituted.Acetylation of 16 followed by catalytic hydrogenolysis gave the crystalline, second title compound.As model compounds for comparative n.m.r. studies, 2-O-, 3-O-, and 6-O-acetyl-D-galactose were also synthesised.
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Doi:10.1248/cpb.32.1313
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