Oxocarbenium ion cyclizations for the synthesis of disaccharide mimetics of 2-amino-2-deoxy-pyranosides: Application to the carbasugar of β-galactosamine-(1,4)-3-O-methyl-D-chiro-inositol

Sunej K Hans; Steven Truong; David R Mootoo

doi:10.1016/j.carres.2022.108595

Oxocarbenium ion cyclizations for the synthesis of disaccharide mimetics of 2-amino-2-deoxy-pyranosides: Application to the carbasugar of β-galactosamine-(1,4)-3-O-methyl-D-chiro-inositol

Carbohydr Res. 2022 Aug:518:108595. doi: 10.1016/j.carres.2022.108595. Epub 2022 May 23.

Authors

Sunej K Hans¹, Steven Truong¹, David R Mootoo²

Affiliations

¹ Department of Chemistry, Hunter College and The Graduate Center of the City University of New York, New York, NY, 10016, USA.
² Department of Chemistry, Hunter College and The Graduate Center of the City University of New York, New York, NY, 10016, USA. Electronic address: [email protected].

PMID: 35643049
DOI: 10.1016/j.carres.2022.108595

Abstract

The synthesis of the carbasugar of β-galactosamine-(1,4)-3-O-methyl-D-chiro-inositol (INS-2), a potential tool for studying glucose metabolism, is described. The synthetic strategy, entails an oxocarbenium ion cyclization on a chiro-inositol derived, thioacetal-enol ether to give a carbocyclic enol ether, which is elaborated to the 2-amino-2-deoxy carbasugar framework via a 2-oximo derivative.

Keywords: 4-C-Lyxose; Carbadisaccharide; Galactosamine; Glycomimetic; Inositol; Insulin.

MeSH terms

Carbasugars*
Cyclization
Disaccharides
Ethers
Galactosamine
Inositol*

Substances

Carbasugars
Disaccharides
Ethers
Inositol
Galactosamine