New stereoselective β-C-glycosidation by uncatalyzed 1,4-addition of organolithium reagents to a glycal-derived vinyl oxirane
New stereoselective β-C-glycosidation by uncatalyzed 1,4-addition of organolithium reagents to a glycal-derived vinyl oxirane
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DOI：
10.1021/ol034662f
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发表时间：
2003-06-12
期刊：
影响因子：
5.2
通讯作者：
Crotti, P
中科院分区：
文献类型：
--
作者：
Di Bussolo, V;Caselli, M;Crotti, P
环氧化物4由D-葡糖醛衍生的羟基甲磺酸酯3原位生成。环氧化物4与一系列烷基和芳基锂试剂反应，得到2，3-不饱和β-C-糖苷，其具有优异的1，4-区域选择性和β-糖苷的完全立体选择性。其他有机金属试剂在与环氧化物4的反应中表现出更复杂的行为。
[GRAPHICS]Epoxide 4 is generated in situ from D-glucal-derived hydroxy mesylate 3. Reaction of epoxide 4 with a series of alkyl- and aryllithium reagents affords 2,3-unsaturated beta-C-glycosides with excellent 1,4-regioselectivity and complete stereoselectivity for the beta-glycoside. Other organometallic reagents demonstrate more complex behavior in their reactions with epoxide 4.