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

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Abstract
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.