Literature DB >> 15959579

Ethyl 2-acetamido-4,6-di-O-benzyl-2,3-N,O-carbonyl-2-deoxy-1-thio-beta-D-glycopyranoside as a versatile GlcNAc donor.

Mike Boysen1, Emiliano Gemma, Martina Lahmann, Stefan Oscarson.   

Abstract

The title donor, ethyl 2-acetamido-4,6-di-O-benzyl-2,3-N,O-carbonyl-2-deoxy-1-thio-beta-D-glycopyranoside, is shown to be an excellent glycosyl donor giving immediate and efficient access to variant GlcNAc-containing oligosaccharides.

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Year:  2005        PMID： 15959579     DOI： 10.1039/b503651h

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  11 in total

1.  Chemoselective synthesis of oligosaccharides of 2-deoxy-2-aminosugars.

Authors:  Aileen F G Bongat; Medha N Kamat; Alexei V Demchenko
Journal:  J Org Chem       Date:  2007-01-25       Impact factor: 4.354

Review 2.  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

3.  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

4.  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

5.  Iterative one-pot syntheses of chitotetroses.

Authors:  Lijun Huang; Zhen Wang; Xiaoning Li; Xin-shan Ye; Xuefei Huang
Journal:  Carbohydr Res       Date:  2006-01-26       Impact factor: 2.104

6.  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

7.  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

8.  Probing the influence of a 4,6-O-acetal on the reactivity of galactopyranosyl donors: verification of the disarming influence of the trans-gauche conformation of C5-C6 bonds.

Authors:  Myriame Moumé-Pymbock; Takayuki Furukawa; Sujit Mondal; David Crich
Journal:  J Am Chem Soc       Date:  2013-09-11       Impact factor: 15.419

9.  Stereocontrolled 1,2-cis glycosylation as the driving force of progress in synthetic carbohydrate chemistry.

Authors:  Swati S Nigudkar; Alexei V Demchenko
Journal:  Chem Sci       Date:  2015-05-01       Impact factor: 9.825

10.  Probing the influence of protecting groups on the anomeric equilibrium in sialic acid glycosides with the persistent radical effect.

Authors:  Pavan K Kancharla; Takayuki Kato; David Crich
Journal:  J Am Chem Soc       Date:  2014-04-01       Impact factor: 15.419
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