Literature DB >> 18374318

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

David Crich1, Feng Cai, Fan Yang.   

Abstract

p-Nitrobenzenesulfenyl chloride is a stable commercially available sulfenyl chloride that, in conjunction with silver triflate, cleanly activates a wide range of thioglycosides for glycosylation at -78 degrees C in CH(2)Cl(2).

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Year:  2008        PMID： 18374318      PMCID： PMC2494598          DOI： 10.1016/j.carres.2008.03.002

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


  15 in total

1.  Iterative one-pot synthesis of oligosaccharides.

Authors:  Xuefei Huang; Lijun Huang; Haisheng Wang; Xin-Shan Ye
Journal:  Angew Chem Int Ed Engl       Date:  2004-10-04       Impact factor: 15.336

2.  Stereoselective alpha-Sialylation with Sialyl Xanthate and Phenylsulfenyl Triflate as a Promotor.

Authors:  Valeri Martichonok; George M. Whitesides
Journal:  J Org Chem       Date:  1996-03-08       Impact factor: 4.354

3.  1-Benzenesulfinyl piperidine/trifluoromethanesulfonic anhydride: a potent combination of shelf-stable reagents for the low-temperature conversion of thioglycosides to glycosyl triflates and for the formation of diverse glycosidic linkages.

Authors:  D Crich; M Smith
Journal:  J Am Chem Soc       Date:  2001-09-19       Impact factor: 15.419

4.  Sulfide-mediated dehydrative glycosylation.

Authors:  H M Nguyen; Y Chen; S G Duron; D Y Gin
Journal:  J Am Chem Soc       Date:  2001-09-12       Impact factor: 15.419

5.  Synthesis of N-unsubstituted, mono- and disubstituted carbohydrate-1-O-carbamates and their behaviour in glycoside syntheses.

Authors:  Hans-Peter Knoben; Urs Schlüter; Hartmut Redlich
Journal:  Carbohydr Res       Date:  2004-12-27       Impact factor: 2.104

6.  Chemistry of 4,6-O-Benzylidene-D-glycopyranosyl Triflates: Contrasting Behavior between the Gluco and Manno Series.

Authors:  David Crich; Weiling Cai
Journal:  J Org Chem       Date:  1999-06-25       Impact factor: 4.354

7.  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

8.  Ph2SO/Tf2O: a powerful promotor system in chemoselective glycosylations using thioglycosides.

Authors:  Jeroen D C Codée; Remy E J N Litjens; René den Heeten; Herman S Overkleeft; Jacques H van Boom; Gijs A van der Marel
Journal:  Org Lett       Date:  2003-05-01       Impact factor: 6.005

9.  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

10.  Stereocontrolled glycoside and glycosyl ester synthesis. neighboring group participation and hydrogenolysis of 3-(2'-benzyloxyphenyl)-3,3-dimethylpropanoates.

Authors:  David Crich; Feng Cai
Journal:  Org Lett       Date:  2007-03-09       Impact factor: 6.005
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  11 in total

1.  Chemical synthesis and functionalization of clickable glycosylphosphatidylinositol anchors.

Authors:  Benjamin M Swarts; Zhongwu Guo
Journal:  Chem Sci       Date:  2011       Impact factor: 9.825

2.  Total synthesis of (+)-sieboldine a: evolution of a pinacol-terminated cyclization strategy.

Authors:  Stephen M Canham; David J France; Larry E Overman
Journal:  J Org Chem       Date:  2012-06-26       Impact factor: 4.354

Review 3.  Chemical synthesis of glycosylphosphatidylinositol anchors.

Authors:  Benjamin M Swarts; Zhongwu Guo
Journal:  Adv Carbohydr Chem Biochem       Date:  2012       Impact factor: 12.200

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.  Versatile set of orthogonal protecting groups for the preparation of highly branched oligosaccharides.

Authors:  Thomas J Boltje; Chunxia Li; Geert-Jan Boons
Journal:  Org Lett       Date:  2010-10-15       Impact factor: 6.005

6.  Stereocontrolled synthesis of D- and L-beta-rhamnopyranosides with 4-O-6-S-alpha-cyanobenzylidene-protected 6-thiorhamnopyranosyl thioglycosides.

Authors:  David Crich; Linfeng Li
Journal:  J Org Chem       Date:  2009-01-16       Impact factor: 4.354

7.  Exploration of the Oxazolidinthione Protecting System for the Synthesis of Sialic Acid Glycosides.

Authors:  Salla Rajender; David Crich
Journal:  J Carbohydr Chem       Date:  2013-09-02       Impact factor: 1.667

8.  Chemical synthesis and immunological evaluation of the inner core oligosaccharide of Francisella tularensis.

Authors:  Thomas J Boltje; Wei Zhong; Jin Park; Margreet A Wolfert; Wangxue Chen; Geert-Jan Boons
Journal:  J Am Chem Soc       Date:  2012-08-16       Impact factor: 15.419

9.  Block synthesis of tetra- and hexasaccharides (beta-D-glycero-D-manno-Hep p-(1-->4)-[alpha-l-Rha p-(1-->3)-beta-D-glycero-D-manno-Hep p-(1-->4)]n-alpha-L-Rha p-OMe (n = 1 and 2)) corresponding to multiple repeat units of the glycan from the surface-layer glycoprotein from Bacillus thermoaerophilus.

Authors:  David Crich; Ming Li
Journal:  J Org Chem       Date:  2008-08-27       Impact factor: 4.354

10.  Capture of uropathogenic E. coli by using synthetic glycan ligands specific for the pap-pilus.

Authors:  Hailemichael O Yosief; Alison A Weiss; Suri S Iyer
Journal:  Chembiochem       Date:  2013-01-10       Impact factor: 3.164
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