Photolabile 2-(2-Nitrophenyl)-propyloxycarbonyl (NPPOC) for Stereoselective Glycosylation and Its Application in Consecutive Assembly of Oligosaccharides

A photolabile protecting group (PPG) 2-(2-nitrophenyl)-propyloxycarbonyl (NPPOC) was explored in glycosylation and applied in the consecutive synthesis of oligosaccharides. NPPOC displays a strong neighboring group participation (NGP) effect to facilitate the construction of 1,2- glycosides in excel...

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Bibliographic Details
Published in:Journal of organic chemistry 2022-03, Vol.87 (5), p.3402-3421
Main Authors: Wang, Jincai, Feng, Yingle, Sun, Taotao, Zhang, Qi, Chai, Yonghai
Format: Article
Language:English
Subjects:
Glycosides
Glycosylation
Oligosaccharides
Photolysis
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Summary:A photolabile protecting group (PPG) 2-(2-nitrophenyl)-propyloxycarbonyl (NPPOC) was explored in glycosylation and applied in the consecutive synthesis of oligosaccharides. NPPOC displays a strong neighboring group participation (NGP) effect to facilitate the construction of 1,2- glycosides in excellent yield. Notably, NPPOC could be efficiently removed by photolysis, and the deprotection conditions are friendly to typical protecting groups. A branched and asymmetric oligomannose Man6 was rapidly prepared, and the consecutive assembly of oligosaccharides without intermediate purification was further investigated owing to the compatibility conditions between NPPPOC's photolysis and glycosylation.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c03006