Selectively protected disaccharide building blocks for modular synthesis of heparin fragments

Michael F. Haller, Geert Jan Boons*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

Abstract

A modular approach for the synthesis of heparin fragments is described. Levulinoyl esters were employed to protect those hydroxy groups intended to be sulfated in the final product, while acetyl esters and benzyl ethers were used as the permanent protecting groups. A highly efficient chemoenzymatic reaction sequence was used for the deprotection of an O-sulfated fragment, while the final stage of the synthesis entailed a selective oxidation of a primary alcohol of a glucoside with TEMPO/NaOCl to give a glucuronic acid moiety.

Original languageEnglish
Pages (from-to)2033-2038
Number of pages6
JournalEuropean Journal of Organic Chemistry
Issue number13
DOIs
Publication statusPublished - 1 Jan 2002
Externally publishedYes

Keywords

  • Carbohydrates
  • Glycosylation
  • Heparin
  • Protecting groups

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