TY - JOUR
T1 - An efficient synthesis of methyl 1,3-O-isopropylidene-α-D- fructofuranoside and 2,3:5,6-di-O-isopropylidene-D-glucose dimethyl acetal derivatives from sucrose
AU - Hanaya, Tadashi
AU - Sato, Nobuaki
AU - Yamamoto, Hiroshi
PY - 2005/11/21
Y1 - 2005/11/21
N2 - Acetalation of sucrose with 2,2-dimethoxypropane in 1,4-dioxane in the presence of p-toluenesulfonic acid, followed by acetylation, afforded methyl 4,6-di-O-acetyl-1,3-O-isopropylidene-α-d-fructofuranoside and 4-O-acetyl-2,3:5,6-di-O-isopropylidene-d-glucose dimethyl acetal as major products, while tosylation of the intermediate acetals provided methyl 6-O-tosyl-1,3-O-isopropylidene-α-d-fructofuranose.
AB - Acetalation of sucrose with 2,2-dimethoxypropane in 1,4-dioxane in the presence of p-toluenesulfonic acid, followed by acetylation, afforded methyl 4,6-di-O-acetyl-1,3-O-isopropylidene-α-d-fructofuranoside and 4-O-acetyl-2,3:5,6-di-O-isopropylidene-d-glucose dimethyl acetal as major products, while tosylation of the intermediate acetals provided methyl 6-O-tosyl-1,3-O-isopropylidene-α-d-fructofuranose.
KW - Acetalation of sucrose
KW - D-Fructofuranoside
KW - D-Glucose dimethyl acetal
KW - Isopropylidene acetal
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U2 - 10.1016/j.carres.2005.07.023
DO - 10.1016/j.carres.2005.07.023
M3 - Article
C2 - 16168975
AN - SCOPUS:26844479243
VL - 340
SP - 2494
EP - 2501
JO - Carbohydrate Research
JF - Carbohydrate Research
SN - 0008-6215
IS - 16
ER -