Studies on the Thioglycosides ofN-Acetylneuraminic Acid. 6: Synthesis of Ganglioside GM4Analogs1

Autor:	Makoto Kiso, Yukiyasu Ito, Akira Hasegawa
Rok vydání:	1989
Předmět:	chemistry.chemical_compound Ceramide Ganglioside chemistry Stereochemistry Organic Chemistry Moiety Selective reduction Azide Biochemistry N-Acetylneuraminic acid
Zdroj:	Journal of Carbohydrate Chemistry. 8:285-294
ISSN:	1532-2327 0732-8303
DOI:	10.1080/07328308908048010
Popis:	Two kinds of ganglioside GM4 thioanalogs having different fatty acyl groups at the ceramide moiety, (2S, 3R, 4E)-1-O-[3-S-(5-acetamido-3,5-di-deoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-3-thio-β-D-galacto-pyranosyl]-2-octadecanamido (or -tetracosanamido)-4-octadecene-1,3-diol (12, 13), have been synthesized. Condensation of the trichloroacetimidate 7, derived from 1,2,4,6-tetra-O-acetyl-3-S-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-3-thio-β-D-galactopyranose (6) by selective 1-O-deacetylation and subsequent trichloroacetimidation, with (2S, 3R, 4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol (4), gave the coupling product (8), which was converted into the title compounds via selective reduction of the azide group, condensation with fatty acids, and removal of the protecting groups.
Databáze:	OpenAIRE
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