Literature DB >> 11405715

Synthesis of the trisaccharide portion of the immunologic adjuvant QS-21A via sulfonium-mediated oxidative and dehydrative glycosylation.

Y J Kim1, D Y Gin.   

Abstract

[see structure]. The first synthesis of the trisaccharide fragment of the potent immunologic adjuvant QS-21A is reported. The key steps involve the application of sulfonium-mediated oxidative and dehydrative glycosidic couplings to construct the anomeric linkages in a short and convergent assembly of the branched trisaccharide.

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Year:  2001        PMID： 11405715     DOI： 10.1021/ol015651u

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


  6 in total

1.  Synthetic studies of complex immunostimulants from Quillaja saponaria: synthesis of the potent clinical immunoadjuvant QS-21Aapi.

Authors:  Yong-Jae Kim; Pengfei Wang; Mauricio Navarro-Villalobos; Bridget D Rohde; JohnMark Derryberry; David Y Gin
Journal:  J Am Chem Soc       Date:  2006-09-13       Impact factor: 15.419

2.  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

Review 3.  Direct Dehydrative Glycosylation of C1-Alcohols.

Authors:  Sloane O'Neill; Jacob Rodriguez; Maciej A Walczak
Journal:  Chem Asian J       Date:  2018-10-01

4.  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 5.  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

6.  Development of Improved Vaccine Adjuvants Based on the Saponin Natural Product QS-21 through Chemical Synthesis.

Authors:  Alberto Fernández-Tejada; Derek S Tan; David Y Gin
Journal:  Acc Chem Res       Date:  2016-08-28       Impact factor: 22.384
  6 in total

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