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

研究成果 › 査読

5 被引用数 (Scopus)

抄録

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.

本文言語	English
ページ（範囲）	2494-2501
ページ数	8
ジャーナル	Carbohydrate Research
巻	340
号	16
DOI	https://doi.org/10.1016/j.carres.2005.07.023
出版ステータス	Published - 11月 21 2005

ASJC Scopus subject areas

分析化学
生化学
有機化学

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10.1016/j.carres.2005.07.023

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「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」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル

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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",

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

language = "English",

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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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