Anomeric stereospecific synthesis of 2′-C-methyl β-nucleosides;: the Holy reaction of cyanamide with 2-C-methyl-D-arabinose

被引：20
|
作者：
Jenkinson, Sarah F.
Jones, Nigel A.
Moussa, Adel
Stewart, Alistair J.
Heinz, Thomas
Fleet, George W. J.
机构：
[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England
[2] Idenix Pharmaceut Inc, Cambridge, MA 02139 USA
[3] Novartis Pharma AG, CH-4002 Basel, Switzerland
来源：
TETRAHEDRON LETTERS | 2007年 / 48卷 / 25期
关键词：
D O I：
10.1016/j.tetlet.2007.04.105
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The sequential reactions of 2-C-methyl-D-arabinose with cyanamide and methyl propiolate afford an anhydronucleoside, which may be opened under acid conditions with inversion at CT, to give 2 degrees-C-methyl uridine; ring opening with sodium hydroxide gave 2'-C-methyl arabino-uridine with retention of configuration at CT. This gives complete stereospecific control to yield only beta-nucleosides. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4441 / 4444
页数：4
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