R. Jeanloz, E. Walker, P. Sinaỹ
Feb 1, 1968
Citations
0
Influential Citations
34
Citations
Journal
Carbohydrate Research
Abstract
Abstract Methyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α- D -glucopyranoside, and methyl, benzyl, and p-nitrophenyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β- D -glucopyranoside were condensed with DL -2-chloropropionic acid to give, in preponderant yields (64, 46, 68, and 25%, respectively), the respective 3-O-( D -1-carboxyethyl) derivatives, separated as their methyl esters. Only from the condensation of the methyl α- D -glucoside was the separation of a significant proportion (11% yield) of the 3-O-( L -1-carboxyethyl) derivative achieved. Acetolysis of methyl 2-acetamido-4,6-di-O-acetyl-2-deoxy-3-O-[( D -1-methoxycarbonyl)ethyl]-α- D -glucopyranoside gave an oxazoline; this was treated with hydrobromic acid in acetic acid, and then with silver oxide and methanol, to give a methyl β- D -glucoside derivative identical with that obtained from methyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β- D -glucopyranoside. Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-[ D -1-(methoxycarbonyl)ethyl]-β- D -glucopyranoside was also obtained by condensation with pure L -chloropropionic acid. Benzyl and p-nitrophenyl 2-acetamido-3-O-( D -1-carboxyethyl)-2-deoxy-β- D -glucopyranoside were resistant to the action of egg-white lysozyme.