Literature DB >> 19643396

Facile synthesis of N-glycosyl amides using a N-glycosyl-2,4-dinitrobenzenesulfonamide and thioacids.

Rommel S Talan1, Aditya K Sanki, Steven J Sucheck.   

Abstract

N-Glucosyl-2,4-dinitrobenzenesulfonamide was prepared from N-acetyl-d-glucosamine and 2,4-dinitrobenzenesulfonyl chloride. Amidation of several thioacids using the N-glucosylsulfonamide donor proceeded smoothly to give the desired N-glucosylamides in good to high yields. The amidation reactions were carried out at room temperature, under mild conditions, and were completed in a very short time.

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Year:  2009        PMID: 19643396     DOI: 10.1016/j.carres.2009.07.002

Source DB:  PubMed          Journal:  Carbohydr Res        ISSN: 0008-6215            Impact factor:   2.104


  4 in total

1.  Mixed-phase synthesis of glycopeptides using a N-peptidyl-2,4-dinitrobenzenesulfonamide-thioacid ligation strategy.

Authors:  Partha Karmakar; Rommel S Talan; Steven J Sucheck
Journal:  Org Lett       Date:  2011-09-14       Impact factor: 6.005

2.  Dihydro-3-(triphenylphosphoranylidene)-2,5-thiophendione: A Convenient Synthon for the Preparation of Substituted 1,4-Thiazepin-5-ones and Piperidinones via the Intermediacy of Thioacids.

Authors:  David Crich; Md Yeajur Rahaman
Journal:  Tetrahedron       Date:  2010-08-14       Impact factor: 2.457

Review 3.  Rethinking amide bond synthesis.

Authors:  Vijaya R Pattabiraman; Jeffrey W Bode
Journal:  Nature       Date:  2011-12-21       Impact factor: 49.962

4.  Synthesis of β-Glycosyl Amides from N-Glycosyl Dinitrobenzenesulfonamides.

Authors:  Vishwanath Gaitonde; Steven J Sucheck
Journal:  J Carbohydr Chem       Date:  2012-07-02       Impact factor: 1.667

  4 in total

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