Synthesis and x-ray crystallographic analysis of 4, 6-di-O-acetyl-2, 3-dideoxy-α-d-threo-hexopyranosyl cyanide. (29th April 2016)

• Record Type: Journal Article
• Authors: Rotella, Madeline; Giovine, Matthew; Dougherty, William; Boyko, Walter; Kassel, Scott; Giuliano, Robert
• Is Part Of: Carbohydrate research. Volume 425(2016)
• Page Start: 40
• Page End: 42
• Publication Date: 2016-04-29
• Subjects: Glycopyranosyl cyanide; Carbohydrates -- Periodicals; Chemistry, Organic -- Periodicals; Biochemistry -- Periodicals; Carbohydrates -- Periodicals; Chimie organique -- Périodiques; Glucides -- Périodiques; Biochemistry; Carbohydrates; Chemistry, Organic; Periodicals; Electronic journals; 507.78
• DOI: 10.1016/j.carres.2016.03.001
• Languages: English
• ISSNs: 0008-6215

Abstract

Highlights: Stereoselective synthesis of a novel glycosyl cyanide. Complete structural assignments based on 2D NMR techniques and x-ray crystallographic analysis. Graphical abstract: Abstract: The glycopyranosyl cyanide 4, 6-di-O-acetyl-2, 3-dideoxy-α-d -threo-hexopyranosyl cyanide has been synthesized from tri-O-acetyl-d -galactal by reaction with trimethylsilyl cyanide in the presence of boron trifluoride diethyl etherate followed by catalytic hydrogenation. The synthesis provides the α-anomer stereoselectively, the structure of which was assigned based on 2D NMR techniques and x-ray crystallography.