SnCl 2 ‐Catalyzed Acetalation/Selective Benzoylation Sequence for the Synthesis of Orthogonally Protected Glycosyl Acceptors

Based on SnCl 2 ‐catalyzed acetalation and selective benzoylation, a one‐pot strategy to efficiently synthesize orthogonally protected glycosyl acceptors with 2‐OH/3‐OH was developed. Consequently, 2‐OBz or 3‐OBz 4,6‐ O ‐benzylidene galactosides and glucosides were efficiently prepared in moderate t...

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Published inEuropean journal of organic chemistry Vol. 2022; no. 33
Main Authors Lv, Jian, Liu, Chun‐Yang, Guo, Yang‐Fan, Feng, Guang‐Jing, Dong, Hai
Format Journal Article
LanguageEnglish
Published 06.09.2022
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Summary:Based on SnCl 2 ‐catalyzed acetalation and selective benzoylation, a one‐pot strategy to efficiently synthesize orthogonally protected glycosyl acceptors with 2‐OH/3‐OH was developed. Consequently, 2‐OBz or 3‐OBz 4,6‐ O ‐benzylidene galactosides and glucosides were efficiently prepared in moderate to high yields starting from free galactosides and glucosides, and were used as valuable glycosyl acceptors for the synthesis of blood group antigens O and B analogues in this study.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202101565