3,5,6-三-氧-甲基-D-葡萄糖与N-取代甘氨酸乙酯反应中的Amadori重排

Amadori Rearrangement in Reaction between 3,5,6-Tri-O-methyl-D-glucose and N-Substituted Glycine Ethyl Ester

Amadori重排是胺(包括氨基酸)与还原糖间一系列复杂反应中的很重要的一步,反应。一级胺以及二级芳香胺与还原糖反应中的Amadori 重排已有大量报道,但对涉及二级脂肪胺特别是 N-取代氨基酸的报道却为数甚少。Anet 曾报道了 N-取代甘氨酸与葡萄糖作用后,得到 Amadori 重排产物的结果,但对其作用机制及反应中间产物无详细描述。本文研究了 N-取代甘氨酸乙酯与3,5,6-三-氧-

Glycine ethyl ester and a-bromoacetophenone react to give N-substituted giycineethyl ester(1).The latter reacts with 3,5,3-tri-O-methyl-O-glucose to (?)yield N-glycoside(2)Which undergoes Amadori reArraNgement in acidic conditioN to form N-2-Phenyl-(?)-oxoethyl)-N-(D-arabino-3,5,6-tri-methoxy-1-hydroxy-(?)-oxohexyl(?)-glycine ethyl este(?) (?)n the otherhand,compound(4),a reaction product of glycine ethyl ester with 3,5,(?).tri-O-methyl-D-glucose,reacts with a-bromoacetophenone to give the same product 3.