Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, USA.
Chem Commun (Camb). 2013 May 14;49(39):4313-5. doi: 10.1039/c2cc35823a. Epub 2012 Sep 19.
Formal synthesis of mycothiol has been developed via nickel-catalyzed α-glycosylation of the C(1)-hydroxyl group of D-myo-inositols with C(2)-N-substituted benzylideneamino N-phenyl trifluoroacetimidate donors. The pseudo-oligosaccharides were obtained in good yield and with excellent α-selectivity. Removal of the C(2)-N-2-trifluoromethylphenyl-benzylidene group under mild conditions provides a pseudo-disaccharide, completing the formal synthesis of mycothiol.
已通过镍催化 D-甘露糖醇 C(1)-位羟基与 C(2)-N-取代的亚苄基氨基 N-苯基三氟乙酰亚胺供体的α-糖苷化反应，开发出了麦硫因的正规合成方法。该假寡糖以较好的产率和优异的α-选择性得到。在温和条件下脱除 C(2)-N-2-三氟甲基苯亚苄基基团，得到假二糖，从而完成了麦硫因的正规合成。
