4141-39-3

Upstream product

• 100-44-7 benzyl chloride 
• 65877-63-6 3-O-benzyl-D-glucopyranose 

Downstream Products

• 76227-09-3 (R)-2-benzyloxy-3-hydroxy-propionaldehyde 
• 76227-13-9 (4R,5R)-5-Benzyloxy-2,4-dihydroxy-tetrahydro-pyran-2-carboxylic acid 

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.