76249-75-7

Upstream product

• 67-56-1 methanol 
• 65877-63-6 3-O-benzyl-D-glucopyranose 
• 100-44-7 benzyl chloride 

Downstream Products

• 87461-26-5 methyl-5-O-benzyl-3-deoxy-α-D-manno-octulopyranoside 
• 87461-27-6 5-O-benzyl-3-deoxy-D-manno-2-octulopyranose 
• 85549-53-7 (2R,4R,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 116390-95-5 methyl (methyl 5-O-benzyl-3-deoxy-7,8-O-isopropylidene-α-D-manno-oct-2-ulopyranosid)onate 4-(diphenyl phosphate) 
• 116464-73-4 methyl (methyl 5-O-benzyl-3-deoxy-7,8-O-isopropylidene-α-D-manno-oct-2-ulopyranosid)onate 

Relevant academic research and scientific papers

Pyranoside Derivatives of 3-Deoxyald-2-ulosonic Acids

At pH 11.5 in 0.2M-sodium tetraborate solution and in the presence of Ni2+, 2-O-benzyl-D-arabinose reacts with oxaloacetic acid to give a 50-60percent yield of 5-O-benzyl-3-deoxyoct-2-ulosonic acids (mixed D-gluco- and D-manno-isomers).The methyl esters of these were separated and the α-methyl glycoside of the D-manno-isomer was prepared.The conformation of the compounds was established by n.m.r. spectroscopy at 250 MHz.It was observed that esterification of the carboxy-group greatly increases the stability of the glycosidic bond of 3-deoxy-D-manno-octulosonic acid while the benzyl substituent in position 5 exerts only a weak stabilising effect. 2-O-Benzyl-D-glyceraldehyde, when treated with oxaloacetic acid in the presence of Ni2+ at pH 7 in the absence of borate, yields 5-O-benzyl-3-deoxyhex-2-ulosonic acids, the predomonant D-erythro-isomer being isolated as its methyl ester.