96236-89-4

Upstream product

• 127-09-3 sodium acetate 
• 100-39-0 benzyl bromide 
• 79189-80-3 3,4,6-tri-O-acetyl-1,2-dideoxy-4'5'-dyhydro-2'<2R-2-hydroxytridecyl>-α-D-glucopyranoso<2,1-d>oxazole 

Downstream Products

• 96236-90-7 allyl 3,4,6-tri-O-acetyl-2-<(3R)-3-benzyloxytetradecanamido>-2-deoxy-β-D-glucopyranoside 

Relevant academic research and scientific papers

CHEMISTRY OF BACTERIAL ENDOTOXINS. PART 3. REACTIONS OF OXAZOLINES DERIVED FROM 1,3,4,6-TETRA-O-ACETYL-2-Β-D-GLUCOPYRANOSE

In acidic medium the oxazoline derived from 2--1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose readily eliminates elements of acetic acid: it is transformed into an oxazoline that carries an olefinic substituent having the E configuration; this compound, when treated with an alcohol, yields the corresponding β-D-glucosaminide.No elimination takes place with the analogous 3-hydroxy- or 3-benzyloxy-tetradecanamidoglucosamine derivatives. (3R)-3-benzyloxy-tetradecanoic acid was obtained in 60percent yield upon treatment of methyl (3R)-3-hydroxytetradecanoate in benzene with benzyl bromide, silver oxide, and anhydrous calcium sulphate, followed by saponification.Under similar conditions 3,4,6-tri-O-acetyl-1,2-dideoxy-4',5'-dihydro-2--α-D-glucopyranosooxazole was transformed into the corresponding (2R)-2-benzyloxyoxazoline.