Chayajarus Kampanart, Chambers David J, Chughtai Majid J, Fairbanks Antony J
The Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK.
Org Lett. 2004 Oct 14;6(21):3797-800. doi: 10.1021/ol048427o.
[reaction: see text] Stereospecific 1,2-cis glycosylation of 2-O-vinyl thioglycosides, synthesized from the corresponding alcohols by Ir-catalyzed transvinylation with vinyl acetate, is achieved by iodine-mediated tethering of a range of primary and secondary carbohydrate acceptors, followed by intramolecular aglycon delivery (IAD). The use of such an intramolecular glycosylation strategy furnishes the desired alpha-gluco and beta-manno disaccharides in an entirely stereoselective manner.
[反应：见正文] 由相应的醇通过铱催化与乙酸乙烯酯进行转乙烯基化反应合成的2-O-乙烯基硫代糖苷的立体专一性1,2-顺式糖基化反应，是通过碘介导一系列伯糖和仲糖受体的连接，然后进行分子内苷元传递（IAD）来实现的。使用这种分子内糖基化策略能以完全立体选择性的方式提供所需的α-葡萄糖和β-甘露糖二糖。
