Literature DB >> 16910646

N-benzyl-2,3-oxazolidinone as a glycosyl donor for selective alpha-glycosylation and one-pot oligosaccharide synthesis involving 1,2-cis-glycosylation.

Shino Manabe1, Kazuyuki Ishii, Yukishige Ito.   

Abstract

Glycosylation reactions using N-benzyl-2,3-trans-oxazolidinones as the glycosyl donors were shown to be highly alpha-selective. Advantages of the donor include facile preparation in gram-scale preparation and simple deprotection procedures. Subsequently, a one-pot oligosaccharide synthesis involving 1,2-cis glycosidic linkages was demonstrated using the novel glycosyl donors.

Entities:  

Year:  2006        PMID: 16910646     DOI: 10.1021/ja062531e

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  20 in total

Review 1.  Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges.

Authors:  Matteo Panza; Salvatore G Pistorio; Keith J Stine; Alexei V Demchenko
Journal:  Chem Rev       Date:  2018-06-28       Impact factor: 60.622

Review 2.  Oligosaccharide Synthesis and Translational Innovation.

Authors:  Larissa Krasnova; Chi-Huey Wong
Journal:  J Am Chem Soc       Date:  2019-02-18       Impact factor: 15.419

3.  Pre-activation Based Stereoselective Glycosylations.

Authors:  Bo Yang; Weizhun Yang; Sherif Ramadan; Xuefei Huang
Journal:  European J Org Chem       Date:  2017-12-28

4.  Recent Advances in Transition Metal-Catalyzed Glycosylation.

Authors:  Matthew J McKay; Hien M Nguyen
Journal:  ACS Catal       Date:  2012-06-14       Impact factor: 13.084

5.  Influence of protecting groups on the anomeric equilibrium; case of the 4,6-O-benzylidene acetal in the mannopyranose series.

Authors:  Indrajeet Sharma; Luis Bohé; David Crich
Journal:  Carbohydr Res       Date:  2012-06-07       Impact factor: 2.104

6.  Facile chemoenzymatic synthesis of biotinylated heparosan hexasaccharide.

Authors:  Baolin Wu; Na Wei; Vireak Thon; Mohui Wei; Zaikuan Yu; Yongmei Xu; Xi Chen; Jian Liu; Peng George Wang; Tiehai Li
Journal:  Org Biomol Chem       Date:  2015-05-14       Impact factor: 3.876

7.  Methodology development and physical organic chemistry: a powerful combination for the advancement of glycochemistry.

Authors:  David Crich
Journal:  J Org Chem       Date:  2011-10-04       Impact factor: 4.354

8.  Dissecting the influence of oxazolidinones and cyclic carbonates in sialic acid chemistry.

Authors:  Pavan K Kancharla; Chandrasekhar Navuluri; David Crich
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-13       Impact factor: 15.336

9.  O-sialylation with N-acetyl-5-n,4-o-carbonyl-protected thiosialoside donors in dichloromethane: facile and selective cleavage of the oxazolidinone ring.

Authors:  David Crich; Wenju Li
Journal:  J Org Chem       Date:  2007-03-06       Impact factor: 4.354

10.  Phenyl 2-amino-N,6-O-dibenzyl-2,3-N,O-carbonyl-2-de-oxy-1-thio-β-d-glucopyran-oside.

Authors:  Shino Manabe; Kazuyuki Ishii; Daisuke Hashizume; Yukishige Ito
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-09-06
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.