52443-08-0

Basic information

• Product Name: 3,4,6-tri-O-acetyl-1,2-O-<(exo and endo)-1-cyanoethylidene>-α-D-galactopyranose
• CAS NO: 52443-08-0
• Molecular Weight: 357.317
• Mol File: 52443-08-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3,4,6-tri-O-acetyl-1,2-O-<(exo and endo)-1-cyanoethylidene>-α-D-galactopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,6-tri-O-acetyl-1,2-O-<(exo and endo)-1-cyanoethylidene>-α-D-galactopyranose(52443-08-0)
• EPA Substance Registry System: 3,4,6-tri-O-acetyl-1,2-O-<(exo and endo)-1-cyanoethylidene>-α-D-galactopyranose(52443-08-0)

Safety Data

• Hazardous Substances Data: 52443-08-0(Hazardous Substances Data)

Upstream product

• 592-04-1 mercury(II) cyanide 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 

Downstream Products

• 73014-31-0 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl cyanide 
• 52443-07-9 3,4,5,7-tetra-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptonitrile 
• 7322-42-1 Acetic acid (2R,3S,4S,5R,6R)-5-acetoxy-2-acetoxymethyl-6-methoxy-4-((3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester 

Relevant articles and documents

Synthesis and characterization of some anomeric pairs of per-O-acetylated aldohexopyranosyl cyanides (per-O-acetylated 2,6-anhydroheptononitriles). On the reaction of per-O-acetylaldohexopyranosyl bromides with mercuric cyanide in nitromethane.

The synthesis and characterization of the anomeric pairs of the per-O-acetylaldohexopyranosyl cyanides of D-galactose, L-fucose, D-glucose, and D-mannose, as well as of 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl cyanide, are described. Cyanation of the readily available, per-O-acetylaldohexopyranosyl bromides with mercuric cyanide in nitromethane, and subsequent purification, gave the corresponding, crystalline glycosyl cyanides with a high degree of 1,2-trans stereoselectivity. Thus, per-O-acetylated aldohexopyranosyl cyanides of the 1,2-trans configuration were obtained in yields ranging from 20 to 79%, whereas the corresponding 1,2-cis anomers were obtained in yields of less than or equal to 8.4%, the ratios of the 1,2-trans:1,2-cis anomers so prepared being greater than or equal to 8.5:1. The principal by-products of these irreversible, cyanation reactions were the per-O-acetylated 1,2-O-[1-(exo- and endo-cyano)ethylidene]aldohexopyranoses, obtained in yields of up to 40%. The structural assignments of the per-O-acetylaldohexopyranosyl cyanides were unequivocally established by elemental analysis, chemical transformation, vibrational spectroscopy, and 13C- and 1H-nuclear magnetic resonance spectroscopy. Correlations between the physical properties and the anomeric configurations of these C-aldohexopyranosyl compounds are described.