新型合成 4,6-O-亚苄基螺[2-脱氧-α-D-阿拉伯己吡喃糖-2,2'-咪唑烷]及其同系物和糖-γ-丁内酰胺衍生物，由 4,6-O-亚苄基-α-D-阿拉伯己吡喃糖-2-酮制备。

Novel synthesis of methyl 4,6-O-benzylidenespiro[2-deoxy-alpha-D-arabino-hexopyranoside-2,2'-imidazolidine] and its homologue and sugar-gamma-butyrolactam derivatives from methyl 4,6-O-benzylidene-alpha-D-arabino-hexopyranosid-2-ulose.

机构信息

Chemistry Department, The Key Lab of Chemical Biology and Organic Chemistry of Henan Province, Zhengzhou University, Zhengzhou, PR China.

出版信息

Carbohydr Res. 2010 Apr 19;345(6):839-43. doi: 10.1016/j.carres.2010.01.004. Epub 2010 Jan 13.

DOI:10.1016/j.carres.2010.01.004

PMID:20138258

Abstract

Novel methyl 4,6-O-benzylidenespiro[2-deoxy-alpha-D-arabino-hexopyranoside-2,2'-imidazolidine] and its homologue methyl 4,6-O-benzylidene-3',4',5',6'-tetrahydro-1'H-spiro[2-deoxy-alpha-D-arabino-hexopyranoside-2,2'-pyrimidine] have been synthesized in good yields by reaction of methyl 4,6-O-benzylidene-alpha-D-arabino-hexopyranosid-2-ulose with 1,2-diaminoethane and 1,3-diaminopropane. The results are completely different from the reaction with arylamines or alkylamines. One-pot synthesis of novel (E)-methyl 4-[hydroxy (methoxy)methylene]-5-oxo-1-alkyl-(4,6-O-benzylidene-2-deoxy-alpha-D-glucopyranosido)[3,2-b]pyrrolidines has been achieved by the reaction of alkylamines with the butenolide-containing sugar, derived from the aldol condensation of methyl 4,6-O-benzylidene-alpha-D-arabino-hexopyranosid-2-ulose with diethyl malonate. These sugar-gamma-butyrolactam derivatives are potential GABA receptor ligands.

摘要

新型甲基 4,6-O-亚苄基螺[2-脱氧-α-D-阿拉伯己呋喃糖-2,2'-咪唑烷]及其同系物甲基 4,6-O-亚苄基-3',4',5',6'-四氢-1'H-螺[2-脱氧-α-D-阿拉伯己呋喃糖-2,2'-嘧啶]通过甲基 4,6-O-亚苄基-α-D-阿拉伯己呋喃糖-2-酮与 1,2-二氨基乙烷和 1,3-二氨基丙烷反应以良好的产率合成。这些结果与芳胺或烷基胺的反应完全不同。通过烷基胺与烯醇内酯糖的反应，一锅法合成了新型（E）-甲基 4-[羟基（甲氧基）亚甲基]-5-氧代-1-烷基-（4,6-O-亚苄基-2-脱氧-α-D-吡喃葡萄糖基）[3,2-b]吡咯烷，该烯醇内酯糖是由甲基 4,6-O-亚苄基-α-D-阿拉伯己呋喃糖-2-酮与丙二酸二乙酯的醛醇缩合反应得到的。这些糖-γ-丁内酰胺衍生物是潜在的 GABA 受体配体。