A Convenient and Chemoselective One-Pot Oxidation/Wittig Reaction for the C2-Homologation of Carbohydrate-Derived Glycols

A simple and convenient one-pot protocol for the chemoselective C2-homologation of carbohydrate-derived glycols is described. The method comprises the chemoselective oxidation of the glycol to the corresponding hydroxyaldehyde and the subsequent Wittig alkenylation. In addition, the method does not...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2005-11, Vol.70 (24), p.10099-10101
Main Authors: Pinacho Crisóstomo, Fernando R, Carrillo, Romen, Martín, Tomás, García-Tellado, Fernando, Martín, Víctor S
Format: Article
Language:English
Subjects:
Carbohydrates - chemistry
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Exact sciences and technology
Glycols - chemical synthesis
Glycols - chemistry
Molecular Conformation
Organic chemistry
Oxidation-Reduction
Preparations and properties
Stereoisomerism
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A simple and convenient one-pot protocol for the chemoselective C2-homologation of carbohydrate-derived glycols is described. The method comprises the chemoselective oxidation of the glycol to the corresponding hydroxyaldehyde and the subsequent Wittig alkenylation. In addition, the method does not need selective protective group manipulation, and it is safe, economical, fast (5 to 6 h), and bench-friendly. Its general utility is discussed.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo051566e