71512-67-9Relevant academic research and scientific papers
REGIOSELECTIVE FORMATION OF DI-O-BENZYL-SUBSTITUTED HEXOPYRANOSIDES VIA STANNYLENE ACETAL INTERMEDIATES
Qin, Huiping,Grindley, T. Bruce
, p. 475 - 490 (2007/10/02)
The reactions of dibutylstannylene acetals derived from several methyl hexopyranosides with benzyl bromide have been investigated.These reactions occur readily in benzyl bromide at 85 deg C.At reaction times of one to two days, the major products are di-O-benzyl derivatives.In several cases, single di-O-benzyl derivatives are the predominant products: methyl α-D-glucopyranoside and methyl β-D-galactopyranoside gave the 2,6- and 3,6-di-O-benzyl ethers in 82 and 70percent yields, respectively.The species present in these reactions and the reaction pathway are discussed.
A Study of the Rapid Anomerization of Poly-O-benzyl-β-D-glucopyranosides with Titanium Tetrachloride
Koto, Shinkiti,Morishima, Naohiko,Kawahara, Reiko,Ishikawa, Katsuhiko,Zen, Shonosuke
, p. 1092 - 1096 (2007/10/02)
Titanium tetrachloride rapidly anomerizes methyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside in dichloromethane at 25 deg C.Evidence for the proposal that the benzyloxymethyl group on C-5 and the ring oxygen of the glucoside cooperate to prompt the reaction is described.The reagent anomerizes the interglycosidic linkage of several disaccharide derivatives.
