TY - JOUR
T1 - Ketone exchange in a sugar bisacetal
AU - Glass, Richard S.
AU - Kwoh, Shuan
AU - Oliveto, Eugene P.
PY - 1973/1
Y1 - 1973/1
N2 - An acid-catalyzed reaction of 2,3:4,6-di-O-isopropylidene-α-l-sorbofuranose with ketones resulted in replacement of the isopropylidene groups with alkylidene groups derived from the ketonic solvent. Kinetically controlled exchange occurs at the 4,6-position. Under equilibrium conditions exchange occurs at the 2,3- as well as the 4,6-position. Participation by the hydroxyl group at C-1 in the rate determining step of exchange at the 2,3-position could not be demonstrated.
AB - An acid-catalyzed reaction of 2,3:4,6-di-O-isopropylidene-α-l-sorbofuranose with ketones resulted in replacement of the isopropylidene groups with alkylidene groups derived from the ketonic solvent. Kinetically controlled exchange occurs at the 4,6-position. Under equilibrium conditions exchange occurs at the 2,3- as well as the 4,6-position. Participation by the hydroxyl group at C-1 in the rate determining step of exchange at the 2,3-position could not be demonstrated.
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U2 - 10.1016/S0008-6215(00)85034-X
DO - 10.1016/S0008-6215(00)85034-X
M3 - Article
AN - SCOPUS:49549171244
VL - 26
SP - 181
EP - 189
JO - Carbohydrate Research
JF - Carbohydrate Research
SN - 0008-6215
IS - 1
ER -