An efficient synthesis of methyl 1,3-O-isopropylidene-alpha-D-fructofuranoside and 2,3:5,6-di-O-isopropylidene-D-glucose dimethyl acetal derivatives from sucrose.
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-alpha-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-alpha-D-fructofuranose.
Hanaya
Tadashi
T
Department of Chemistry, Faculty of Science, Okayama University, Tsushima, Okayama 700-8530, Japan. hanaya@cc.okayama-u.ac.jp
Sato
Nobuaki
N
Yamamoto
Hiroshi
H
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D005632:Fructose / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D005947:Glucose / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013395:Sucrose / Q000737:chemistry*
D000475:Alkenes; D005632:Fructose; D013395:Sucrose; C013658:propylene; D005947:Glucose