Enantiopure 4-deoxypentenosides, dihydropyrans and tetrahydropyrans and syntheses thereof

US7521568B2 · kind B2 · utility

Assignee

• Purdue Research Foundation · US

Inventors

• Alexander Wei · Wilnsdorf, DE
• Fabien P. Boulineau · Lafayette, US

Key dates

• Filing date: Dec 13, 2002
• Grant date: Apr 21, 2009
• Expiry date: Oct 9, 2025

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07B2200/07
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Enantiopure substituted 4-deoxypentenosides (4-DPs) and related dihydropyrans (DHPs) are prepared from common carbohydrates via a novel process. The 4-DPs and related DHPs are amenable to a broad range of stereoselective transformations and are used as synthetic intermediates to prepare a variety of enantiopure tetrahydropyrans (THPs), including rare or exotic sugars and other complex THPs of commercial or medicinal value. In one embodiment of the instant invention, 4-DPs are converted to L-sugars in a novel process that offers distinct advantages over known synthetic methods.