Direct Synthesis of para-Nitrophenyl Glycosides from Reducing Sugars in Water

被引：22

作者：

Qiu, Xin ^{[1
]}

Fairbanks, Antony J. ^{[1
,2
]}

机构：

[1] Univ Canterbury, Sch Phys & Chem Sci, Christchurch 8140, New Zealand

[2] Univ Canterbury, Biomol Interact Ctr, Christchurch 8140, New Zealand

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 06期

关键词：

ONE-POT SYNTHESIS; 2-CHLORO-1,3-DIMETHYLIMIDAZOLINIUM CHLORIDE; UNPROTECTED SUGARS; GLYCOPEPTIDES; ACTIVATION;

D O I：

10.1021/acs.orglett.0c00728

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reducing sugars may be directly converted into the corresponding para-nitrophenyl (pNP) glycosides using 2-chloro-1,3-dimethylimidazolinium chloride (DMC), para-nitrophenol, and a suitable base in aqueous solution. The reaction is stereoselective for sugars with either a hydroxyl or an acetamido group at position 2, yielding the 1,2-trans pNP glycosides. A judicious choice of base allows extension to di- and oligosaccharide substrates, including a complex N-glycan oligosaccharide isolated from natural sources, without the requirement of any protecting group manipulations

引用

页码：2490 / 2493

页数：4

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