Synthesis of a useful anomeric thioacetate of an N-acetyllactosamine derivative and its application

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• 作者：Matsuoka ; Koji ; Ohtawa ; Takumi ; Hinou ; Hiroshi ; Koyama ; Tetsuo ; Esumi ; Yasuaki ; Nishimura ; Shin-Ichiro ; et. al.
• 关键词：N-acetyllactosamine ; glycosides ; thioacetic acid ; thioacetates ; glycoclusters
• 刊名：Tetrahedron Letters
• 出版年：2003
• 出版时间：April 28, 2003
• 年：2003
• 卷：44
• 期：18
• 页码：3617-3620
• 全文大小：183 K

文摘

A novel anomeric β-thioacetate of an N-acetyllactosamine derivative was efficiently synthesized in high yield from the known 2-azido glycosyl chloride using thioacetic acid as a convenient reagent. The synthesis involved not only an S_N2 replacement of the chloride by a carbothiolate anion but also a reductive acetamidation of the azide group. Applications of the thioacetate for glycosidation were demonstrated to provide both O- and S-glycosides in high yields. Furthermore, both intermediates gave a new class of glycoclusters that included thioglycosidic linkages.