Straightforward route for anchoring a glucosyl moiety onto nucleophilic species: reaction of amines and alcohols with carboxymethyl 3,4,6-tri-O-acetyl-alpha-D-glucopyranoside 2-O-lactone

Stéphane Trombotto; Mathieu Danel; Juliette Fitremann; Alain Bouchu; Yves Queneau

doi:10.1021/jo0300237

Straightforward route for anchoring a glucosyl moiety onto nucleophilic species: reaction of amines and alcohols with carboxymethyl 3,4,6-tri-O-acetyl-alpha-D-glucopyranoside 2-O-lactone

J Org Chem. 2003 Aug 22;68(17):6672-8. doi: 10.1021/jo0300237.

Authors

Stéphane Trombotto¹, Mathieu Danel, Juliette Fitremann, Alain Bouchu, Yves Queneau

Affiliation

¹ Unité Mixte de Sucrochimie CNRS-Béghin-Say (UMR 143), C/o Béghin-Say, C.E.I., 27 boulevard du 11 novembre 1918, B.P. 2132, 69603 Villeurbanne Cedex, France.

PMID: 12919031
DOI: 10.1021/jo0300237

Abstract

The base-catalyzed reaction of carboxymethyl 3,4,6-tri-O-acetyl-alpha-D-glucopyranoside 2-O-lactone (prepared from isomaltulose) with amino acids and fatty amines under basic catalysis gave a series of new pseudoglucopeptides, nonionic amphiphiles, and polymerizable derivatives. The same reaction applied to alcohols provided the corresponding 2-(alpha-D-glucopyranosyloxy)acetyl esters with either basic or acidic catalysts.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alcohols / chemistry
Alkenes / chemical synthesis*
Alkenes / chemistry
Amines / chemistry
Carbohydrate Conformation
Glucose*
Indicators and Reagents
Lactones / chemical synthesis*
Lactones / chemistry
Models, Molecular
Optical Rotation

Substances

Alcohols
Alkenes
Amines
Indicators and Reagents
Lactones
alkolactone A
Glucose