D-氨基葡萄糖合成3-苯甲酰胺基-5-乙酰基呋喃  

Synthesis of 3-Benzamide-5-acetyl Furan from D-glucosamine

作　　者：杨棕楠 朱聪 朱丹丹 徐玲 杨森 赵丽颖 周兰兰 曹志凌 YANG Zong-nan;ZHU Cong;ZHU Dan-dan;XU Ling;YANG Sen;ZHAO Li-ying;ZHOU Lan-lan;CAO Zhi-ling(College of Pharmacy, Jiangsu Ocean University, Lianyungang 222005, China)

机构地区：[1]江苏海洋大学药学院,江苏连云港222005

出　　处：《合成化学》2021年第1期81-84,共4页Chinese Journal of Synthetic Chemistry

基　　金：国家自然科学基金资助项目(21402062);江苏高校优势学科建设工程项目(PAPD);江苏省研究生科研与实践创新项目(KYCX18-2582,KYCX19-2280,SJCX20-1225,SJCX20-1232)。

摘　　要：以可再生D-氨基葡萄糖为底物,在甲醇/三乙胺体系中,以苯甲酰氯作为酰化试剂,经选择性N-酰化反应合成得N-苯甲酰基-D-氨基葡萄糖(3),继续在硼酸催化下,转化为3-苯甲酰胺基-5-乙酰基呋喃(4),两步一锅煮总产率44%,其结构经1H NMR,13C NMR,IR和MS(ESI)确证。Renewable biobased D-glucosamine was used as the raw material for the synthesis of 3-benzamide-5-acetyl furan.First,N-benzoyl glucosamine was synthesized by selective N-acylation of D-glucosamine(3)in methanol-triethylamine system with benzoyl chloride as the acylating reagent.Then,N-benzoyl-D-glucosamine(3)was converted to 3-benzamide-5-acetyl furan(4)by microwave irradiation in the presence of boric acid catalyst.The total yield over two-reactions in one pot was 44%and the structure of the title compound was confirmed by 1H NMR,13C NMR,IR and MS(ESI)spectroscopy.

关 键 词：氨基葡萄糖 合成 N-(5-乙酰呋喃)-苯甲酰胺 β-氨基呋喃 微波 

分 类 号：O623.6[理学—有机化学] O626[理学—化学]