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- Title
Reagent Control of a Birch Reduction for the Synthesis of a 2-Deoxyoligosaccharide Possessing a 1,4-Dialkylhydroquinone.
- Authors
Yamaguchi, Sho; Tanaka, Hiroshi; Takahashi, Takashi
- Abstract
We have developed a versatile deprotection method for the synthesis of 2-deoxyoligosaccharides containing a 1,4-dialkylhydroquinone moiety at the anomeric position. The Birch reduction of a 2,6-dideoxy monosaccharide with potassium and 1,3-pentadiene gave the deprotected product without any undesired reduction. The utility of this method was then demonstrated in the Birch reduction of a landomycin E deoxytrisaccharide. Pd-catalysed hydrogenation led to the anomerization, or cleavage, of the glycosidic linkages. In contrast, Birch reduction based on the optimized conditions followed by treatment with mCPBA ( m-chloroperoxybenzoic acid) provided the fully deprotected deoxytrisaccharide in 65 % overall yield. These results show that the Birch reduction is a powerful deprotection method for the synthesis of complex natural glycosides, including 2-deoxyoligosaccharides.
- Subjects
OLIGOSACCHARIDE synthesis; GLYCOSIDE synthesis; HYDROQUINONE; BIRCH reduction; POTASSIUM; PENTADIENES; HYDROGENATION
- Publication
European Journal of Organic Chemistry, 2015, Vol 2015, Issue 22, p4939
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201500515