A versatile approach to the synthesis of glycans containing mannuronic acid residues

被引：9

作者：

Alex, Catherine ^{[1
]}

Visansirikul, Satsawat ^{[1
,2
]}

Demchenko, Alexei, V ^{[1
]}

机构：

[1] Univ Missouri, Dept Chem & Biochem, One Univ Blvd, St Louis, MO 63121 USA

[2] Mahidol Univ, Fac Pharm, Dept Pharmaceut Chem, 447 Sri Ayuddhaya Rd, Bangkok 10400, Thailand

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2021年 / 19卷 / 12期

关键词：

D O I：

10.1039/d1ob00188d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reported herein is a new method for a highly effective synthesis of beta-glycosides from mannuronic acid donors equipped with the 3-O-picoloyl group. The stereocontrol of glycosylations was achieved by means of the H-bond-mediated aglycone delivery (HAD). The method was utilized for the synthesis of a tetrasaccharide linked via beta-(1 -> 3)-mannuronic linkages. We have also investigated 3,6-lactonized glycosyl donors that provided moderate to high beta-manno stereoselectivity in glycosylations. A method to achieve complete alpha-manno stereoselectivity with mannuronic acid donors equipped with 3-O-benzoyl group is also reported.

引用

页码：2731 / 2743

页数：13

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