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

Tadashi Hanaya, Nobuaki Sato, Hiroshi Yamamoto

Research output: Contribution to journal › Article

5 Citations (Scopus)

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 languageEnglish
Pages (from-to)2494-2501
Number of pages8
JournalCarbohydrate Research
Volume340
Issue number16
DOIs
Publication statusPublished - Nov 21 2005

Fingerprint

Sucrose
Derivatives
Glucose
Acetylation
Acetals
1,1-dimethoxyethane
propylene
2,2-dimethoxypropane
4-toluenesulfonic acid
1,4-dioxane

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

Hanaya, T, Sato, N & Yamamoto, H 2005, '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', Carbohydrate Research, vol. 340, no. 16, pp. 2494-2501. https://doi.org/10.1016/j.carres.2005.07.023
Hanaya T, Sato N, Yamamoto H. 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. Carbohydrate Research. 2005 Nov 21;340(16):2494-2501. https://doi.org/10.1016/j.carres.2005.07.023
Hanaya, Tadashi ; Sato, Nobuaki ; Yamamoto, Hiroshi. / 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. In: Carbohydrate Research. 2005 ; Vol. 340, No. 16. pp. 2494-2501.
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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.

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