Literature DB >> 20136154

Regioselective control in the oxidative cleavage of 4,6-O-benzylidene acetals of glycopyranosides by dimethyldioxirane.

Arnaud Stévenin1, François-Didier Boyer, Jean-Marie Beau.   

Abstract

The oxidative cleavage of 4,6-O-benzylidene acetals of glycopyranosides using dimethyldioxirane (DMDO) leads to the corresponding hydroxy-benzoates in excellent yields. With a proper choice of the neighboring protecting groups, this oxidative fragmentation provides the 6- or 4-hydroxyl derivatives in a highly regioselective manner.

Entities:  

Year:  2010        PMID: 20136154     DOI: 10.1021/jo9026098

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  4 in total

1.  Stereoelectronic factors in the stereoselective epoxidation of glycals and 4-deoxypentenosides.

Authors:  Laura Alberch; Gang Cheng; Seung-Kee Seo; Xuehua Li; Fabien P Boulineau; Alexander Wei
Journal:  J Org Chem       Date:  2011-03-18       Impact factor: 4.354

2.  HPLC-Based Automated Synthesis of Glycans in Solution.

Authors:  Samira Escopy; Yashapal Singh; Keith J Stine; Alexei V Demchenko
Journal:  Chemistry       Date:  2022-05-25       Impact factor: 5.020

3.  Palladium(II)-assisted activation of thioglycosides.

Authors:  Samira Escopy; Yashapal Singh; Alexei V Demchenko
Journal:  Org Biomol Chem       Date:  2021-03-11       Impact factor: 3.876

4.  A Streamlined Regenerative Glycosylation Reaction: Direct, Acid-Free Activation of Thioglycosides.

Authors:  Samira Escopy; Yashapal Singh; Keith J Stine; Alexei V Demchenko
Journal:  Chemistry       Date:  2020-11-30       Impact factor: 5.236

  4 in total

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