Direct Synthesis of the β-L-rhamnopyranosides
Direct Synthesis of the β-L-rhamnopyranosides
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DOI：
10.1021/ol0340890
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发表时间：
2003-03-06
期刊：
影响因子：
5.2
通讯作者：
Picione, J
中科院分区：
文献类型：
--
作者：
Crich, D;Picione, J
[图表]报道了通过用2-O-磺酸酯和理想的4-O-苯甲酰基酯保护的硫代糖苷供体直接形成β-L-吡喃鼠李糖苷。在2，4，6-三叔丁基嘧啶存在下，用1-苯亚磺酰基哌啶和三氟甲磺酸酐的组合实现活化。选择性从中等到良好不等，并且磺酰基在用2-丙醇中的汞齐进行糖基化后容易除去。
[GRAPHICS]The direct formation Of beta-L-rhamnopyranosides by means of thioglycoside donors protected with a 2-O-sulfonate ester and, ideally, a 4-O-benzoyl ester, is reported. Activation is achieved with the combination of 1-benzenesulfinyl piperidine and triflic anhydride in the presence of 2,4,6-tri-tert-butylpyrimidine. Selectivities vary from moderate to good, and the sulfonyl group is easily removed post-glycosylation with sodium amalgam in 2-propanol.