Literature DB >> 14535720

Efficient sialylation with phenyltrifluoroacetimidates as leaving groups.

Sutang Cai1, Biao Yu.   

Abstract

[reaction: see text] Sialylation with N-phenyltrifluoroacetimidates as leaving groups and a catalytic amount of TMSOTf as promoter compares favorably with the previous protocols for direct sialylation and expand in essence the scope of the Schmidt glycosylation reaction.

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Year:  2003        PMID： 14535720     DOI： 10.1021/ol0353161

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


  10 in total

1.  Chemical Synthesis of a Glycopeptide Derived from Skp1 for Probing Protein Specific Glycosylation.

Authors:  Zoeisha S Chinoy; Christopher M Schafer; Christopher M West; Geert-Jan Boons
Journal:  Chemistry       Date:  2015-07-15       Impact factor: 5.236

Review 2.  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

3.  Scalable synthesis of Fmoc-protected GalNAc-threonine amino acid and T(N) antigen via nickel catalysis.

Authors:  Fei Yu; Matthew S McConnell; Hien M Nguyen
Journal:  Org Lett       Date:  2015-04-08       Impact factor: 6.005

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.  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.  Pre-activation-based one-pot synthesis of an alpha-(2,3)-sialylated core-fucosylated complex type bi-antennary N-glycan dodecasaccharide.

Authors:  Bin Sun; Balasubramanian Srinivasan; Xuefei Huang
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

7.  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

8.  Studies on the selectivity between nickel-catalyzed 1,2-cis-2-amino glycosylation of hydroxyl groups of thioglycoside acceptors with C2-substituted benzylidene N-phenyl trifluoroacetimidates and intermolecular aglycon transfer of the sulfide group.

Authors:  Fei Yu; Hien M Nguyen
Journal:  J Org Chem       Date:  2012-08-09       Impact factor: 4.354

9.  Halogen-directed chemical sialylation: pseudo-stereodivergent access to marine ganglioside epitopes.

Authors:  Taiki Hayashi; Alexander Axer; Gerald Kehr; Klaus Bergander; Ryan Gilmour
Journal:  Chem Sci       Date:  2020-03-26       Impact factor: 9.825

10.  Automated synthesis of sialylated oligosaccharides.

Authors:  Davide Esposito; Mattan Hurevich; Bastien Castagner; Cheng-Chung Wang; Peter H Seeberger
Journal:  Beilstein J Org Chem       Date:  2012-09-21       Impact factor: 2.883
  10 in total

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