Guidelines for O-Glycoside Formation from First Principles

被引：68

作者：

Andreana, Peter R. ^{[1
,2
]}

Crich, David ^{[3
,4
,5
]}

机构：

[1] Univ Toledo, Dept Chem & Biochem, Toledo, OH 43606 USA

[2] Univ Toledo, Sch Green Chem & Engn, Toledo, OH 43606 USA

[3] Univ Georgia, Dept Pharmaceut & Biomed Sci, Athens, GA 30602 USA

[4] Univ Georgia, Dept Chem, Athens, GA 30602 USA

[5] Univ Georgia, Complex Carbohydrate Res Ctr, Athens, GA 30602 USA

来源：

ACS CENTRAL SCIENCE | 2021年 / 7卷 / 09期

关键词：

NUCLEOPHILIC-SUBSTITUTION; GLYCOSYLATION REACTIONS; CHEMICAL GLYCOSYLATION; DIPHENYLMETHYL BROMIDE; BETA-MANNOSYLATION; ORGANIC-CHEMISTRY; PROTECTING GROUPS; ARALKYL SYSTEMS; MECHANISMS; REACTIVITY;

D O I：

10.1021/acscentsci.1c00594

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The complexity and irreproducibility of glycosylation reactions retard progress the glycosciencs. Application of the steady-state hypothesis to transient oxocarbenium ion-counterion pair intermediates reveals the importance of concentration, temperature, and other factors in glycosylation stereoselectivity. Guidelines are then adduced for the practice of O-glycosylation reactions on the oasis of which more reproducible, practical protocols can be established.

引用

页码：1454 / 1462

页数：9

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