96236-90-7Relevant 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
Diolez, Christian,Sarfati, S. Robert,Szabo, Ladislas
, p. 57 - 60 (2007/10/02)
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.
