An efficient short-step total synthesis of ganglioside GM 3: effective usage of the neighbouring group participation strategy

T Tomoo, T Kondo, H Abe, S Tsukamoto, M Isobe…

文献索引：Tomoo, Toshiyuki; Kondo, Tadao; Abe, Hiroyuki; Tsukamoto, Syunji; Isobe, Minoru; Goto, Toshio Carbohydrate Research, 1996 , vol. 284, # 2 p. 207 - 222

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被引用次数: 35

摘要

We have developed an efficient methodology for highly stereoselective sialylation using 3- position substituted sialic acids and have prepared 2a having a 3β-phenylthio group as a sialic donor. Glycosylation of suitably protected lactoside 3 with 2a gave only the α-sialyl trisaccharide 16 in good yield. Condensation of the azidosphingosine 4 with the acetate 17 using promotors, DMTST or NIS-TfOH, afforded the glycolipid 18, which was directly ...