Large-scale synthesis of 6-deoxy-6-sulfonatomethyl glycosides and their application for novel synthesis of a heparinoid pentasaccharide trisulfonic acid of anticoagulant activity

Erika Mezo, Mihály Herczeg, Dániel Eszenyi, A. Borbás

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Multigram-scale syntheses of three 6-deoxy-6-sulfonatomethyl α-glucosides were accomplished via reactions of the corresponding primary triflate derivatives with the lithiated ethyl methanesulfonate. Chemoselective glycosylation reactions of different 6-C-sulfonatomethyl glucoside donors were studied. The sulfonic acid-containing building blocks were utilised in a novel [2+3] block synthesis of a trisulfonic acid isoster of the anticoagulant pentasaccharide idraparinux.

Original languageEnglish
Pages (from-to)19-29
Number of pages11
JournalCarbohydrate Research
Volume388
Issue number1
DOIs
Publication statusPublished - Mar 31 2014

Fingerprint

Heparinoids
Glucosides
Glycosides
Anticoagulants
Ethyl Methanesulfonate
Glycosylation
Acids
Sulfonic Acids
Derivatives

Keywords

  • Aglycon transfer
  • Anticoagulation
  • Chemoselective glycosylation
  • Pentasaccharide
  • Sulfonic acid
  • Uronic acids

ASJC Scopus subject areas

  • Biochemistry
  • Analytical Chemistry
  • Organic Chemistry

Cite this

Large-scale synthesis of 6-deoxy-6-sulfonatomethyl glycosides and their application for novel synthesis of a heparinoid pentasaccharide trisulfonic acid of anticoagulant activity. / Mezo, Erika; Herczeg, Mihály; Eszenyi, Dániel; Borbás, A.

In: Carbohydrate Research, Vol. 388, No. 1, 31.03.2014, p. 19-29.

Research output: Contribution to journalArticle

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AU - Borbás, A.

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