Standard Article

Zemplén Deacetylation

(Zemplén De-O-acetylation, Zemplén Transesterification, Zemplén Deprotection)

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr691

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Zemplén Deacetylation. Comprehensive Organic Name Reactions and Reagents. 691:3123–3128.

Publication History

  1. Published Online: 15 SEP 2010

Chemistry Terms

Choose one or more boxes to highlight terms.

Abstract

The efficient removal of the O-acetyl protecting groups of carbohydrates by treatment of the O-acetylated substrates in methanol with a catalytic amount of sodium methoxide at room temperature is generally known as the Zemplén deacetylation, Zemplén de-O-acetylation, or Zemplen deacetylation. In addition, after the reaction, the O-acetyl-protected carbohydrates are transformed into unprotected ones, in a manner analogous to the hydrolysis of an ester, thus this reaction is termed as the Zemplen saponification as well. However, it has been reported that the Zemplén deacetylation is probably not suitable for the deprotection of carbohydrates with disulfide linkages. This reaction has wide applications in carbohydrate chemistry.

Keywords:

  • sodium methoxide;
  • O-acetyl-protected carbohydrate;
  • β-D-glucose pentaacetate;
  • carbohydrate