Literature DB >> 12841775

Dehydrative sialylation with C2-hemiketal sialyl donors.

Jannine M Haberman1, David Y Gin.   

Abstract

[reaction: see text] A new method for sialylation involving the dehydrative coupling of sialyl donors with the reagent combination of (p-nitrophenyl)(phenyl) sulfoxide and triflic anhydride is reported. This process establishes sialyl C2-hemiketals as viable sialyl donors for complex carbohydrate synthesis.

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Year:  2003        PMID： 12841775     DOI： 10.1021/ol034815z

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  10 in total

Review 1.  Advances in the biology and chemistry of sialic acids.

Authors:  Xi Chen; Ajit Varki
Journal:  ACS Chem Biol       Date:  2010-02-19       Impact factor: 5.100

2.  Stereoselective Synthesis of the Equatorial Glycosides of Legionaminic Acid.

Authors:  Oskar Popik; Bibek Dhakal; David Crich
Journal:  J Org Chem       Date:  2017-06-02       Impact factor: 4.354

3.  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

4.  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

5.  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

6.  Efficient glycosidation of a phenyl thiosialoside donor with diphenyl sulfoxide and triflic anhydride in dichloromethane.

Authors:  David Crich; Wenju Li
Journal:  Org Lett       Date:  2006-03-02       Impact factor: 6.005

Review 7.  Chemical glycosylation in the synthesis of glycoconjugate antitumour vaccines.

Authors:  Danica P Galonić; David Y Gin
Journal:  Nature       Date:  2007-04-26       Impact factor: 49.962

8.  Imposing the trans/gauche conformation on a sialic acid donor with a 5-N,7-O-oxazinanone group: effect on glycosylation stereoselectivity.

Authors:  David Crich; Baolin Wu
Journal:  Tetrahedron       Date:  2008-02-25       Impact factor: 2.457

9.  Mechanistic studies on a sulfoxide transfer reaction mediated by diphenyl sulfoxide/triflic anhydride.

Authors:  Martin A Fascione; Sophie J Adshead; Pintu K Mandal; Colin A Kilner; Andrew G Leach; W Bruce Turnbull
Journal:  Chemistry       Date:  2012-01-31       Impact factor: 5.236

Review 10.  Mechanistic Investigations into the Application of Sulfoxides in Carbohydrate Synthesis.

Authors:  Martin A Fascione; Robin Brabham; W Bruce Turnbull
Journal:  Chemistry       Date:  2016-01-07       Impact factor: 5.236
  10 in total

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