Clean conversion of D-glucosamine hydrochloride to a pyrazine in the presence of phenylboronate or borate

Citation
J. Rohovec et al., Clean conversion of D-glucosamine hydrochloride to a pyrazine in the presence of phenylboronate or borate, EUR J ORG C, (20), 2001, pp. 3899-3901
Citations number
17
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
20
Year of publication
2001
Pages
3899 - 3901
Database
ISI
SICI code
1434-193X(200110):20<3899:CCODHT>2.0.ZU;2-1
Abstract
D-Glucosamine was found to undergo a condensation to give 2-(arabo-tetrahyd roxybutyl)-5-(erythro-2,3,4-trihydroxybutyl)-pyrazine (2) as practically th e sole product in the presence of phenylboronate or borate. The reaction pr oceeds in aqueous solutions at room temperature in 3 h in 58% isolated yiel d. In D2O solutions, the incorporation of one deuterium into the methylene group of the trihydroxybutyl arm was found. The borate esters of the produc t were investigated by B-11 and C-13 NMR spectroscopy.