Stereoselective synthesis of aryl 1,2-cis-furanosides and its application to the synthesis of the carbohydrate portion of antibiotic hygromycin A

被引：9
|
作者：
Xu, Yuan
Bin, Hua-Chao
Su, Fu
Yang, Jin-Song [1 ]
机构：
[1] Sichuan Univ, Dept Chem Med Nat Prod, Chengdu 610041, Peoples R China
来源：
TETRAHEDRON LETTERS | 2017年 / 58卷 / 16期
关键词：
Furanoside; Hygromycin A; Glycosylation; Synthesis; Thioglycoside; Stereoselectivity; SEMISYNTHETIC MODIFICATION; ANTIBACTERIAL ACTIVITY; A SYNTHESIS; NUCLEOSIDE ANTIBIOTICS; AMINOCYCLITOL ANALOGS; GLYCOSYL DONORS; A201A; HOMOMYCIN; OXIDATION; RELEVANT;
D O I：
10.1016/j.tetlet.2017.02.079
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient methodology for the synthesis of aryl 1,2-cis-furanosidic linkages has been developed with 2-quinolinecarbonyl (Quin) group substituted furanose ethyl thioglycosides as glycosyl donors. The method permits a wide range of phenol acceptors to be used, thus resulting in the formation of structurally diverse phenol furanosides in good to excellent chemical yields with complete 1,2-cis anomeric selectivity. The synthetic utility of the approach has been demonstrated by concise preparation of the carbohydrate portion of antibiotic hygromycin A. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1548 / 1552
页数：5
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