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KMID : 1059519980420010078
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Journal of the Korean Chemical Society
1998 Volume.42 No. 1 p.78 ~ p.83
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A Facile Synthesis of Disacharides Containing α-Altropyranosidic Linkage by 1,2-trans Glycosidation of D-allal Derivatives
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Choi Jong-Lak
Yoon Shin-Sook
Chun Keun-Ho
Nam Jeong-E
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Abstract
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It's necessary to develope a facile methodology forming α-altropyranosidic linkage, for the synthesis of trisaccharide repeating unit of O-antigenic part of Campylobacter jejuni gram negative bacteria. In this paper, the effective synthesis of disaccharides containing α-altropyranosidic linkage by 1,2-trans glycosidation of allal derivatives was discussed. 4, 6-O-Benzylidene-3-O-(t-butyldimethylsilyl)-D-allal was treated with DMDO (3,3-dimethy ldioxirane) to yield 1,2-anhydro-4, 6-O-benzylidene-3-O-(t-butyldimethylsilyl)-β-D-altropyranose. The reaction of 1,2-anhydro-4, 6-O-benzylidene-3-O-(t-butyldimethylsilyl)-β-D-altropyranose with allyl alcohol gave allyl 4, 6-O-benzylidene-3-(t-butyldimethylsilyl)-α-D-altropyranoside quantitatively, and reactions with glucals were also successful to prepare α-altropyranosodic disaccharides. It is convinced that 1,2-trans glycosidation of allal derivatives should be an attractive choice for preparing oligosaccharides containing α-altropyranosidic linkages.
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