Abstract
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.
Original language | English |
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Pages (from-to) | 2494-2501 |
Number of pages | 8 |
Journal | Carbohydrate Research |
Volume | 340 |
Issue number | 16 |
DOIs | |
Publication status | Published - Nov 21 2005 |
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Keywords
- Acetalation of sucrose
- D-Fructofuranoside
- D-Glucose dimethyl acetal
- Isopropylidene acetal
ASJC Scopus subject areas
- Biochemistry
- Molecular Biology
- Organic Chemistry
Cite this
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. / Hanaya, Tadashi; Sato, Nobuaki; Yamamoto, Hiroshi.
In: Carbohydrate Research, Vol. 340, No. 16, 21.11.2005, p. 2494-2501.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - An efficient synthesis of methyl 1,3-O-isopropylidene-α-D- fructofuranoside and 2,3
T2 - 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
UR - http://www.scopus.com/inward/record.url?scp=26844479243&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=26844479243&partnerID=8YFLogxK
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 -