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
收藏
页码：2731 / 2743
页数：13
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