59464-22-1

Basic information

• Product Name: 1,6-anhydro-2-azido-2-deoxy-3,4-di-O-benzyl-β-D-galactopyranose
• Synonyms: 1,6-anhydro-2-azido-2-deoxy-3,4-di-O-benzyl-β-D-galactopyranose
• CAS NO: 59464-22-1
• Molecular Weight: 367.404
• Mol File: 59464-22-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1,6-anhydro-2-azido-2-deoxy-3,4-di-O-benzyl-β-D-galactopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6-anhydro-2-azido-2-deoxy-3,4-di-O-benzyl-β-D-galactopyranose(59464-22-1)
• EPA Substance Registry System: 1,6-anhydro-2-azido-2-deoxy-3,4-di-O-benzyl-β-D-galactopyranose(59464-22-1)

Safety Data

• Hazardous Substances Data: 59464-22-1(Hazardous Substances Data)

Upstream product

• 65371-89-3 1,6-anhydro-3,4-O-isopropylidene-2-azido-2-deoxy-β-D-galactopyranose 
• 21193-75-9 D-galactal 
• 161254-77-9 1,6-anhydro-2-deoxy-2-iodo-β-D-galactopyranose 
• 79781-69-4 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-galactopyranose 
• 81353-38-0 (trimethylsilylethynyl)tributyltin 
• 79781-68-3 1-O-acetyl-2-azido-3,4,6-tri-O-benzyl-2-desoxy-D-galactopyranose 
• 67313-36-4 1,6-anhydro-2-azido-2-deoxy-β-D-galactopyranose 
• 100-39-0 benzyl bromide 

Downstream Products

• 104139-57-3 1,6-anhydro-3,4-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranose 
• 67313-39-7 1,6-di-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-galactopyranose 

Relevant articles and documents

Investigation of the hydrogen bonding properties of a series of monosaccharides in aqueous media by 1H NMR and IR spectroscopy

A technique, based on 1H NMR and IR experiments, to characterise intramolecular hydrogen bonds in aqueous medium in a series of amino, amido and ammonium sugar derivatives has been established. Three groups of molecules, representing amides (4, 5 and 6), amines (7 and 8) and ammonium salts (chlorides 9 and 10, and phosphates 11 and 12), with different relative configurations of their functional groups, have been investigated to assess the effect of the nature and the stereochemistry of these groups on the hydrogen-bonding features of the sugar. The deduced features in water solution are compared to those obtained previously in nonpolar solvents. The phosphate salts of amines 7 and 8 (11 and 12) were also prepared, in order to evaluate the influence of the OH groups on the binding of the phosphate counterion, and the possibility of establishing cooperative hydrogen bonds involving the phosphate group. The data presented here indicate that the 1,3-cis-diaxial-type configuration in sugar diols and amino alcohols produces an intramolecular six-membered-ring hydrogen bond that survives in water and, moreover, offers the possibility to establish cooperative intermolecular hydrogen bonds. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Synthesis of α-Glycopyranosides of D-Galactosamine and D-Glucosamine via Iodocyclization of Corresponding Glycals and Silver Tetrafluoroboranuide-Promoted Alkynylation at the Anomeric Centre

Iodocyclization of O-stannylated D-galactal 1, followed by azide ion displacement, gave 1,6-anhydro-2-azido-2-deoxy-β-D-galactopyranose 9 in a expeditious way.Transformation into bromide 12 allowed coupling of various alkynyltributylstannanes in the presence of silver tetrafluoroboranuide (silver tetrafluoroborate), thus affording the corresponding α,β-C-(D-galactopyranosyl)alkynes 13 - 17.Application of this methodology to the D-gluco isomeric bromide 24 gave a C-(D-glucopyranosyl)octyne 25 with total α-stereoselectivity.Conventional deprotection and saturation of the acetylenic linkage led to C-octyl-α-glycopyranosides of D-galactosamine 20 and D-glucosamine 28.