Ph2SO/Tf2O:: a powerful promotor system in chemoselective glycosylations using thioglycosides

Ph2SO/Tf2O:: a powerful promotor system in chemoselective glycosylations using thioglycosides
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DOI:
10.1021/ol034312t
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发表时间:
2003-05-01
期刊:
影响因子:
5.2
通讯作者:
van der Marel, GA
van der Marel, GA
中科院分区:
化学1区
文献类型:
--
作者:
Codée, JDC;Litjens, REJN;van der Marel, GA

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【图形】二苯亚砜与三氟甲磺酸酐结合可提供一种非常有效的亲硫糖基化促进剂体系,能够活化无武装(钝化)的硫代糖苷。这种新型亲硫活化剂的有效性在一个成功的化学选择性糖基化序列中得到了体现,在该序列中,第一步缩合反应中的供体硫代糖苷可以是有武装(活化)的,也可以是无武装(钝化)的。
[GRAPHICS]Diphenylsulfoxide in combination with triflic anhydride provides a very potent thiophilic glycosylation promotor system, capable of activating disarmed thioglycosides. The usefulness of this novel thiophilic activator is illustrated in a successful chemoselective glycosylation sequence in which the donor thioglycoside in the first condensation step may be either armed or disarmed.