The first chemical synthesis of 6-thio-d-fructo-pyranose via methyl 6-bromo-6-deoxy-1,3-o-isopro-pylidene-α-d-fructofuranoside as a key intermediate

Tadashi Hanaya; Nobuaki Sato; Hiroshi Yamamoto

doi:10.3987/COM-06-10965

The first chemical synthesis of 6-thio-d-fructo-pyranose via methyl 6-bromo-6-deoxy-1,3-o-isopro-pylidene-α-d-fructofuranoside as a key intermediate

Tadashi Hanaya, Nobuaki Sato, Hiroshi Yamamoto

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

Abstract

Selective bromination of sucrose, followed by acetalation with 2,2-dimethoxypropane in 1,4-dioxane in the presence of p-toluenesulfonic acid, afforded methyl 6-bromo-6-deoxy-1,3-O-isopropylidene-α-d-fructofuranoside (4). The first chemical synthesis of 6-thio-d-fructopyranose was accomplished from 4 through its 6-S-acetyl-6-thio derivative.

Original language	English
Pages (from-to)	517-522
Number of pages	6
Journal	Heterocycles
Volume	71
Issue number	3
DOIs	https://doi.org/10.3987/COM-06-10965
Publication status	Published - Mar 1 2007

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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title = "The first chemical synthesis of 6-thio-d-fructo-pyranose via methyl 6-bromo-6-deoxy-1,3-o-isopro-pylidene-α-d-fructofuranoside as a key intermediate",

abstract = "Selective bromination of sucrose, followed by acetalation with 2,2-dimethoxypropane in 1,4-dioxane in the presence of p-toluenesulfonic acid, afforded methyl 6-bromo-6-deoxy-1,3-O-isopropylidene-α-d-fructofuranoside (4). The first chemical synthesis of 6-thio-d-fructopyranose was accomplished from 4 through its 6-S-acetyl-6-thio derivative.",

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

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doi = "10.3987/COM-06-10965",

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AU - Hanaya, Tadashi

AU - Sato, Nobuaki

AU - Yamamoto, Hiroshi

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N2 - Selective bromination of sucrose, followed by acetalation with 2,2-dimethoxypropane in 1,4-dioxane in the presence of p-toluenesulfonic acid, afforded methyl 6-bromo-6-deoxy-1,3-O-isopropylidene-α-d-fructofuranoside (4). The first chemical synthesis of 6-thio-d-fructopyranose was accomplished from 4 through its 6-S-acetyl-6-thio derivative.

AB - Selective bromination of sucrose, followed by acetalation with 2,2-dimethoxypropane in 1,4-dioxane in the presence of p-toluenesulfonic acid, afforded methyl 6-bromo-6-deoxy-1,3-O-isopropylidene-α-d-fructofuranoside (4). The first chemical synthesis of 6-thio-d-fructopyranose was accomplished from 4 through its 6-S-acetyl-6-thio derivative.

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The first chemical synthesis of 6-thio-d-fructo-pyranose via methyl 6-bromo-6-deoxy-1,3-o-isopro-pylidene-α-d-fructofuranoside as a key intermediate

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