Synthetic Route to 2-Deoxyaldoses by Fluoride-Catalyzed Solvolysis of Enol-Phosphate Esters

Naoki Mitsuo; Yoshihiro Abe; Takeo Takizawa; Takehisa Kunieda

doi:10.1248/cpb.28.1327

Synthetic Route to 2-Deoxyaldoses by Fluoride-Catalyzed Solvolysis of Enol-Phosphate Esters

Naoki Mitsuo, Yoshihiro Abe, Takeo Takizawa, Takehisa Kunieda

School of Pharmacy

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

2 Citations (Scopus)

Abstract

1-Alkenyl and phenyl phosphate esters undergo smooth cleavage of the phosphorus-oxygen linkage by fluoride-catalyzed alcoholysis to give aldehydes (ketones) and phenols, respectively. Application of this method provides a new route to 2-deoxyaldosugars from the enol-phosphates derived from vinylene carbonate telomers.

Original language	English
Pages (from-to)	1327-1330
Number of pages	4
Journal	Chemical and Pharmaceutical Bulletin
Volume	28
Issue number	4
DOIs	https://doi.org/10.1248/cpb.28.1327
Publication status	Published - 1980

Keywords

2-deoxyaldose
aryl phosphate
cesium fluoride
enol phosphate
vinylene carbonate telomer

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

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10.1248/cpb.28.1327

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abstract = "1-Alkenyl and phenyl phosphate esters undergo smooth cleavage of the phosphorus-oxygen linkage by fluoride-catalyzed alcoholysis to give aldehydes (ketones) and phenols, respectively. Application of this method provides a new route to 2-deoxyaldosugars from the enol-phosphates derived from vinylene carbonate telomers.",

keywords = "2-deoxyaldose, aryl phosphate, cesium fluoride, enol phosphate, vinylene carbonate telomer",

author = "Naoki Mitsuo and Yoshihiro Abe and Takeo Takizawa and Takehisa Kunieda",

year = "1980",

doi = "10.1248/cpb.28.1327",

language = "English",

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pages = "1327--1330",

journal = "Chemical and Pharmaceutical Bulletin",

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publisher = "Pharmaceutical Society of Japan",

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T1 - Synthetic Route to 2-Deoxyaldoses by Fluoride-Catalyzed Solvolysis of Enol-Phosphate Esters

AU - Mitsuo, Naoki

AU - Abe, Yoshihiro

AU - Takizawa, Takeo

AU - Kunieda, Takehisa

PY - 1980

Y1 - 1980

N2 - 1-Alkenyl and phenyl phosphate esters undergo smooth cleavage of the phosphorus-oxygen linkage by fluoride-catalyzed alcoholysis to give aldehydes (ketones) and phenols, respectively. Application of this method provides a new route to 2-deoxyaldosugars from the enol-phosphates derived from vinylene carbonate telomers.

AB - 1-Alkenyl and phenyl phosphate esters undergo smooth cleavage of the phosphorus-oxygen linkage by fluoride-catalyzed alcoholysis to give aldehydes (ketones) and phenols, respectively. Application of this method provides a new route to 2-deoxyaldosugars from the enol-phosphates derived from vinylene carbonate telomers.

KW - 2-deoxyaldose

KW - aryl phosphate

KW - cesium fluoride

KW - enol phosphate

KW - vinylene carbonate telomer

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IS - 4

ER -

Synthetic Route to 2-Deoxyaldoses by Fluoride-Catalyzed Solvolysis of Enol-Phosphate Esters

Abstract

Keywords

ASJC Scopus subject areas

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