Preparation of 1-C-glycosyl aldehydes by reductive hydrolysis

Szabolcs Sipos, István Jablonkai

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Reductive hydrolysis of various protected glycosyl cyanides was carried out using DIBAL-H to form aldimine alane intermediates which were then hydrolyzed under mildly acidic condition to provide the corresponding aldehyde derivatives. While 1-C-formyl glycal and 2-deoxy glycosyl derivatives were stable during isolation and storage 1-C-glycosyl formaldehydes in the gluco, galacto and manno series were sensitive and decomposition occurred by 2-alkyloxy elimination. A one-pot method using N,N′-diphenylethylenediamine to trap these aldehydes in stable form was developed. Reductive hydrolysis of glycosyl cyanides offers valuable aldehyde building blocks in a convenient way which can be applied in the synthesis of complex C-glycosides.

Original languageEnglish
Pages (from-to)1503-1510
Number of pages8
JournalCarbohydrate Research
Volume346
Issue number12
DOIs
Publication statusPublished - Sep 6 2011

Keywords

  • 1,3-Imidazolidine derivative
  • 1-C-Glycosyl aldehydes
  • DIBAL-H
  • Glycosyl cyanides
  • β-Elimination

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Preparation of 1-C-glycosyl aldehydes by reductive hydrolysis'. Together they form a unique fingerprint.

  • Cite this