82266-99-7

Upstream product

• 89158-09-8 2,3,4-tri-O-acetyl-1-deoxy-1-bromo-α-D-arabinopyranosyl cyanide 

Downstream Products

• 352310-79-3 3,4,5-tri-O-acetyl-2,6-anhydro-D-glycero-D-manno-hexose tosylhydrazone 

Relevant academic research and scientific papers

PREPARATION OF 1,2-CIS-GLYCOSYL CYANIDES BY THE STEREOSELECTIVE REDUCTION OF ACETYLATED 1-BROMO-D-GLYCOSYL CYANIDES

Reductive dehalogenation of acetylated 1-bromo-D-glycosyl cyanides with tri-n-butyltin hydride favours the formation of 1,2-trans-glycosyl cyanides, while reactions with zinc-acetic acid, zinc-isopropanol, and sodium borohydride give 1,2-cis-glycosyl cyanides as the major product.

Preparation of 2,6-Anhydro-3-deoxyhept-(or hex-)2-enononitriles (1-Cyanoglycals) from 1-Bromo-D-glycosyl Cyanides with Zinc under Aprotic Conditions

Acetylated 1-bromo-D-glycosyl cyanides 1 - 5 react with zinc dust in acetic acid, acetic acid/water, or 2-propanol to give mixtures of acetylated 1-cyanoglycals 6-9 and anomeric pairs of glycosyl cyanides 10-14.Reaction of 1-5 in refluxing benzene in the presence of one equivalent of triethylamine or especially pyridine predominantly leads to the formation of 1-cyanoglycals.