Literature DB >> 15357583

Interhalogens (ICl/IBr) and AgOTf in thioglycoside activation; synthesis of bislactam analogues of ganglioside GD3.

Andréas Meijer1, Ulf Ellervik.   

Abstract

The novel promoter system IX/AgOTf (X = Cl or Br) has been evaluated in the synthesis of two bislactam analogues of GD3. We have carried out two high-yielding galactosylations in 97% and 98% yield, respectively, using ICl/AgOTf, and four sialylations in 93%, 59%, 40%, and 44% yield, using IBr/AgOTf. The choice of interhalogen (IX) is determined by the donor type used in the glycosylation. We also report some mechanistic investigations leading to further optimization of the IX/AgOTf promoter system.

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Year:  2004        PMID： 15357583     DOI： 10.1021/jo049184g

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  5 in total

Review 1.  The Experimental Evidence in Support of Glycosylation Mechanisms at the SN1-SN2 Interface.

Authors:  Philip Ouma Adero; Harsha Amarasekara; Peng Wen; Luis Bohé; David Crich
Journal:  Chem Rev       Date:  2018-05-30       Impact factor: 60.622

2.  Synthesis and intramolecular glycosylation of sialyl mono-esters of o-xylylene glycol. The importance of donor configuration and nitrogen protecting groups on cyclization yield and selectivity; isolation and characterization of a N-sialyl acetamide indicative of participation by acetonitrile.

Authors:  Harsha Amarasekara; David Crich
Journal:  Carbohydr Res       Date:  2016-10-08       Impact factor: 2.104

3.  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

4.  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

5.  Synthesis of a tetra- and a trisaccharide related to an anti-tumor saponin "Julibroside J28" from Albizia julibrissin.

Authors:  Bimalendu Roy; Kausikisankar Pramanik; Balaram Mukhopadhyay
Journal:  Glycoconj J       Date:  2007-08-16       Impact factor: 2.916
  5 in total

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