Hydrogen bond-assisted 1,2-cis O-glycosylation under mild hydrogenolytic conditions

[Display omitted] A hydrogen bond-assisted α-selective glycosylation reaction by using 4,6-dibenzyloxy-1,3,5-triazin-2-yl (DBT) β-glycosyl donors was developed for the efficient construction of 1,2-cis-α-glycosidic bond in natural products. This method was applied successfully to the direct synthesi...

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Bibliographic Details
Published inChinese chemical letters Vol. 34; no. 4; p. 107754
Main Authors Li, Gefei, Luo, Yanlong, Mo, Juan, Noguchi, Masato, Jing, Jie, Luo, Zhenyang, Shoda, Shin-ichiro, Ye, Xin-Shan
Format Journal Article
LanguageEnglish
Published Elsevier B.V 01.04.2023
Subjects
Glycolipid
Hydrogen bond
Natural product
O-Glycosylation
α-Selectivity
Natural product
α-Selectivity
O-Glycosylation
Hydrogen bond
Glycolipid
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Summary:[Display omitted] A hydrogen bond-assisted α-selective glycosylation reaction by using 4,6-dibenzyloxy-1,3,5-triazin-2-yl (DBT) β-glycosyl donors was developed for the efficient construction of 1,2-cis-α-glycosidic bond in natural products. This method was applied successfully to the direct synthesis of complex oligosaccharide-derived glycolipids with simple protecting chemistry. Mechanistic studies using the NMR spectroscopy and DFT calculation provide a proof of concept for hydrogen bond-assisted glycosylation reaction towards α-specific construction of O-glycosidic linkage.
ISSN:1001-8417
1878-5964
DOI:10.1016/j.cclet.2022.107754