Literature DB >> 11535081

Sulfide-mediated dehydrative glycosylation.

H M Nguyen1, Y Chen, S G Duron, D Y Gin.   

Abstract

The development of a new method for glycosylation with 1-hydroxy glycosyl donors employing dialkyl sulfonium reagents is described. The process employs the reagent combination of a dialkyl sulfide and triflic anhydride to effect anomeric bond constructions. This controlled dehydrative coupling of various C(1)-hemiacetal glycosyl donors and nucleophilic acceptors proceeds by way of a sulfide-to-sulfoxide oxidation process in which triflic anhydride serves as the oxidant.

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Year:  2001        PMID: 11535081     DOI: 10.1021/ja015968p

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


  19 in total

1.  Immobilization of glycans on solid surfaces for application in glycomics.

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Journal:  J Carbohydr Chem       Date:  2018-04-27       Impact factor: 1.667

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.  Superarming the S-benzoxazolyl glycosyl donors by simple 2-O-benzoyl-3,4,6-tri-O-benzyl protection.

Authors:  Laurel K Mydock; Alexei V Demchenko
Journal:  Org Lett       Date:  2008-05-01       Impact factor: 6.005

4.  Synthesis and structure verification of the vaccine adjuvant QS-7-Api. Synthetic access to homogeneous Quillaja saponaria immunostimulants.

Authors:  Kai Deng; Michelle M Adams; David Y Gin
Journal:  J Am Chem Soc       Date:  2008-04-15       Impact factor: 15.419

5.  An Improved Approach to the Direct Construction of 2-Deoxy-β-Linked Sugars: Applications to Oligosaccharide Synthesis.

Authors:  Dina Lloyd; Clay S Bennett
Journal:  Chemistry       Date:  2018-05-02       Impact factor: 5.236

6.  S-Benzimidazolyl (SBiz) Imidates as a Platform for Oligosaccharide Synthesis via Active-Latent, Armed-Disarmed, Selective, and Orthogonal Activations.

Authors:  Scott J Hasty; Mithila D Bandara; Nigam P Rath; Alexei V Demchenko
Journal:  J Org Chem       Date:  2017-02-07       Impact factor: 4.354

7.  Facile Synthesis of Sugar Lactols via Bromine-Mediated Oxidation of Thioglycosides.

Authors:  Shuai Meng; Bishwa Raj Bhetuwal; Padam P Acharya; Jianglong Zhu
Journal:  J Carbohydr Chem       Date:  2019-03-20       Impact factor: 1.667

8.  Application of the superarmed glycosyl donor to chemoselective oligosaccharide synthesis.

Authors:  Laurel K Mydock; Alexei V Demchenko
Journal:  Org Lett       Date:  2008-05-01       Impact factor: 6.005

9.  A stable, commercially available sulfenyl chloride for the activation of thioglycosides in conjunction with silver trifluoromethanesulfonate.

Authors:  David Crich; Feng Cai; Fan Yang
Journal:  Carbohydr Res       Date:  2008-03-10       Impact factor: 2.104

10.  Electrochemical generation of glycosyl triflate pools.

Authors:  Toshiki Nokami; Akito Shibuya; Hiroaki Tsuyama; Seiji Suga; Albert A Bowers; David Crich; Jun-ichi Yoshida
Journal:  J Am Chem Soc       Date:  2007-08-14       Impact factor: 15.419

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