Chemical approaches for the stereocontrolled synthesis of 1,2-cis-β-D-rhamnosides

被引：1

作者：

Cai, Juntao ^{[1
]}

Yuan, Xin ^{[1
]}

Kong, Yuanfang ^{[2
]}

Hu, Yulong ^{[1
]}

Li, Jieming ^{[1
]}

Jiang, Shiqing ^{[1
,3
]}

Dong, Chunhong ^{[1
]}

Ding, Kan ^{[1
,4
]}

机构：

[1] Henan Univ Chinese Med, Henan Key Lab Chinese Med Polysaccharides & Drugs, Henan Polysaccharide Res Ctr, Acad Chinese Med Sci, Zhengzhou 450046, Peoples R China

[2] Henan Univ Chinese Med, Coll Pharm, Zhengzhou 450046, Peoples R China

[3] Henan Univ Chinese Med, Affiliated Hosp 1, Zhengzhou 450000, Henan, Peoples R China

[4] Chinese Acad Sci, Shanghai Inst Mat Med, Carbohydrate Based Drug Res Ctr, CAS Key Lab Receptor Res,State Key Lab Drug Res, Shanghai 201203, Peoples R China

来源：

CHINESE JOURNAL OF NATURAL MEDICINES | 2023年 / 21卷 / 12期

关键词：

Carbohydrate; Glycosylation; 1,2-cis-Glycoside; Stereoselectivity; Total synthesis; /I-Rhamnoside; REDUCTIVE RADICAL FRAGMENTATION; TRISACCHARIDE REPEATING UNIT; O-SPECIFIC POLYSACCHARIDE; BETA-D-RHAMNOPYRANOSIDES; STEREOSELECTIVE-SYNTHESIS; VERSATILE APPROACH; GLYCOSYL DONORS; D-RHAMNOSIDES; LIPOPOLYSACCHARIDE; XANTHOMONAS;

D O I：

10.1016/S1875-5364(23)60408-X

中图分类号：

R [医药、卫生];

学科分类号：

10 ;

摘要：

In carbohydrate chemistry, the stereoselective synthesis of 1,2-cis-glycosides remains a formidable challenge. This complexity is comparable to the synthesis of 1,2-cis-/I-D-mannosides, primarily due to the adverse anomeric and Delta-2 effects. Over the past decades, to attain /I-stereoselectivity in D-rhamnosylation, researchers have devised numerous direct and indirect methodologies, including the hydrogen-bond-mediated aglycone delivery (HAD) method, the synthesis of /I-D-mannoside paired with C6 deoxygenation, and the combined approach of 1,2-trans-glycosylation and C2 epimerization. This review elaborates on the advancements in /I-D-rhamnosylation and its implications for the total synthesis of tiacumicin B and other physiologically relevant glycans.

引用

页码：886 / 901

页数：16

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