Publication Type
Publication Type
Peer Reviewed Journal
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Authors
Garegg, Per J.,Hultberg, Hans,Oscarson, Stefan;
Year
1982
Month
Journal
Title
A regioselective reductive ring opening of 4,6-O-prop-2-enylidene acetals of hexopyranosides
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Published
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Volume
Issue
10
Start Page
2395
End Page
7
Abstract
The propenylidene acetals I (R = PhCH2O, R1 = OMe; R = NHAc, R1 = OCH2Ph) and II underwent regioselective reductive cleavage on treatment with NaBH3CN and HCl in THF at room temp. to give the a-D-glucopyranosides III (R = R1 = PhCH2O, R2 = OMe; R = R2 = PhCH2O, R1 = NHAc) and the b-D-galactopyranoside III (R = R1 = BzO, R2 = OMe) in 74, 79, and 84% yield, resp. The method gives ready access to protected hexopyranose moieties with a free 4-OH group. [on SciFinder (R)]
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