Concise syntheses of D-desosamine, 2-thiopyrimidinyl desosamine donors, and methyl desosaminide analogues from D-glucose
Concise syntheses of D-desosamine, 2-thiopyrimidinyl desosamine donors, and methyl desosaminide analogues from D-glucose
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DOI：
10.1016/j.carres.2007.10.004
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发表时间：
2008-01-14
影响因子：
3.1
通讯作者：
Andrade, Rodrigo B.
中科院分区：
文献类型：
--
作者：
Velvadapu, Venkata;Andrade, Rodrigo B.
以甲基α-D-吡喃葡萄糖苷为原料，经五步反应合成D-氨基葡萄糖，总收率15%。然后将Desosamine转化为两种已知的2-硫代嘧啶基供体（Woodward和Tatsuta供体），每种都分两步进行。最后，从常见的2，3-脱水糖中间体制备C-3位的甲基desosaminide的类似物（3-吡咯烷基、3-哌啶基、3-吗啉基）。(c)2007爱思唯尔有限公司保留所有权利。
A concise synthesis of D-desosamine has been accomplished in five steps and in 15% overall yield from methyl alpha-D-gluco-pyranoside. Desosamine was then transformed into two known 2-thiopyrimidinyl donors (Woodward and Tatsuta donors), each in two steps. Finally, analogues of methyl desosaminide at the C-3 position were prepared (3-pyrrolidino, 3-piperidino, 3-morpholino) from a common 2,3-anhydrosugar intermediate. (c) 2007 Elsevier Ltd. All rights reserved.