Transformation of D-glucose into 1D-3-deoxy-3-hydroxymethyl-myo-inositol by stereocontrolled intramolecular Henry reaction

Raquel G Soengas; Juan C Estévez; Ramón J Estévez

doi:10.1021/ol035771x

Transformation of D-glucose into 1D-3-deoxy-3-hydroxymethyl-myo-inositol by stereocontrolled intramolecular Henry reaction

Org Lett. 2003 Nov 13;5(23):4457-9. doi: 10.1021/ol035771x.

Authors

Raquel G Soengas¹, Juan C Estévez, Ramón J Estévez

Affiliation

¹ Departamento de Química Orgánica, Universidade de Santiago, 15782 Santiago de Compostela, Spain.

PMID: 14602024
DOI: 10.1021/ol035771x

Abstract

[reaction: see text] An intramolecular Henry cyclization provides a promising new strategy for the transformation of nitroheptofuranoses into deoxyhydroxymethylinositols. This method has allowed a stereospecific transformation of d-glucose into 1D-3-deoxy-3-hydroxymethyl-myo-inositol.

Publication types

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

MeSH terms

Glucose / metabolism*
Inositol / analogs & derivatives*
Inositol / chemistry*
Stereoisomerism

Substances

1D-3-deoxy-3-hydroxymethyl-myo-inositol
Inositol
Glucose