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Studies on the Thioglycosides ofN-Acetyl-Neuraminic Acid 8: Synthesis of S-(α-Sialyl)-(2→ 6)-β-Hexopyranosyl and -(2→ 6')-β-Lactosyl Ceramides Containing β-Thioglycosidically Linked Ceramide

 

作者: Akira Hasegawa,   Hirotsugu Ogawa,   Makoto Kiso,  

 

期刊: Journal of Carbohydrate Chemistry  (Taylor Available online 1991)
卷期: Volume 10, issue 6  

页码: 1009-1021

 

ISSN:0732-8303

 

年代: 1991

 

DOI:10.1080/07328309108543969

 

出版商: Taylor & Francis Group

 

数据来源: Taylor

 

摘要:

Coupling of the sodium salt ofS-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-galacto-2-nonulopyranosylonate)-(2→'6)-2,3,4-tri-O-acetyl-1,6-dithio-β-D-glucopyranose (5), -β-D-galactopyranose (8), orS-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2→'6)-O-(2,3,4-tri-O-acetyl-6-thio-β-D-galactopyranosyl)-(1→'4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranose (12), which were prepared from the corresponding 1-hydroxy compounds,1, 2, and9,via1-chlorination, displacement with thioacetyl group, andS-deacetylation, with (2S,3R,4E)-2-azido-3-O-benzoyl-1-O-(p-toluenesulfonyl)-4-octadecene-1,3-diol (13), gave the corresponding β-thioglycosides14, 18and22, respectively in good yields. The β-thioglycosides obtained were converted,viaselective reduction of the azide group, condensation with octadecanoic acid, and removal of the protecting groups, into the title compounds.

 

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