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

doi:10.1016/j.carres.2005.07.023

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

Institute for Education and Student Services

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	2494-2501
Number of pages	8
Journal	Carbohydrate Research
Volume	340
Issue number	16
DOIs	https://doi.org/10.1016/j.carres.2005.07.023
Publication status	Published - Nov 21 2005

Keywords

Acetalation of sucrose
D-Fructofuranoside
D-Glucose dimethyl acetal
Isopropylidene acetal

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Organic Chemistry

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@article{f2c5a166a0af4fbbaf784aa7d5140dda,

title = "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",

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.",

keywords = "Acetalation of sucrose, D-Fructofuranoside, D-Glucose dimethyl acetal, Isopropylidene acetal",

author = "Tadashi Hanaya and Nobuaki Sato and Hiroshi Yamamoto",

year = "2005",

month = nov,

day = "21",

doi = "10.1016/j.carres.2005.07.023",

language = "English",

volume = "340",

pages = "2494--2501",

journal = "Carbohydrate Research",

issn = "0008-6215",

publisher = "Elsevier BV",

number = "16",

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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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DO - 10.1016/j.carres.2005.07.023

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