Stereoselectivity in deoxygenation of 5-hydroxy-5-phosphinyl-hexofuranoses (α-hydroxyphosphonates)

Tadashi Hanaya; Ken Ichi Sugiyama; Heizan Kawamoto; Hiroshi Yamamoto

doi:10.1016/S0008-6215(03)00235-0

Stereoselectivity in deoxygenation of 5-hydroxy-5-phosphinyl-hexofuranoses (α-hydroxyphosphonates)

Tadashi Hanaya, Ken Ichi Sugiyama, Heizan Kawamoto, Hiroshi Yamamoto

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20 Citations (Scopus)

Abstract

The addition of dimethyl phosphonate to six different hexofuranos-5-uloses in the presence of DBU, followed by esterification with methoxalyl chloride and then radical reduction, afforded 5-deoxy-5-dimethoxyphosphinyl-D- and L-hexofuranoses. The stereoselectivity of the deoxygenation and possible transition-state models are discussed.

Original language	English
Pages (from-to)	1641-1650
Number of pages	10
Journal	Carbohydrate Research
Volume	338
Issue number	16
DOIs	https://doi.org/10.1016/S0008-6215(03)00235-0
Publication status	Published - Jul 29 2003

Keywords

Deoxygenation
Phospho sugar
α-Hydroxyphosphonate

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Organic Chemistry

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10.1016/S0008-6215(03)00235-0

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title = "Stereoselectivity in deoxygenation of 5-hydroxy-5-phosphinyl-hexofuranoses (α-hydroxyphosphonates)",

abstract = "The addition of dimethyl phosphonate to six different hexofuranos-5-uloses in the presence of DBU, followed by esterification with methoxalyl chloride and then radical reduction, afforded 5-deoxy-5-dimethoxyphosphinyl-D- and L-hexofuranoses. The stereoselectivity of the deoxygenation and possible transition-state models are discussed.",

keywords = "Deoxygenation, Phospho sugar, α-Hydroxyphosphonate",

author = "Tadashi Hanaya and Sugiyama, {Ken Ichi} and Heizan Kawamoto and Hiroshi Yamamoto",

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doi = "10.1016/S0008-6215(03)00235-0",

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pages = "1641--1650",

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T1 - Stereoselectivity in deoxygenation of 5-hydroxy-5-phosphinyl-hexofuranoses (α-hydroxyphosphonates)

AU - Hanaya, Tadashi

AU - Sugiyama, Ken Ichi

AU - Kawamoto, Heizan

AU - Yamamoto, Hiroshi

PY - 2003/7/29

Y1 - 2003/7/29

N2 - The addition of dimethyl phosphonate to six different hexofuranos-5-uloses in the presence of DBU, followed by esterification with methoxalyl chloride and then radical reduction, afforded 5-deoxy-5-dimethoxyphosphinyl-D- and L-hexofuranoses. The stereoselectivity of the deoxygenation and possible transition-state models are discussed.

AB - The addition of dimethyl phosphonate to six different hexofuranos-5-uloses in the presence of DBU, followed by esterification with methoxalyl chloride and then radical reduction, afforded 5-deoxy-5-dimethoxyphosphinyl-D- and L-hexofuranoses. The stereoselectivity of the deoxygenation and possible transition-state models are discussed.

KW - Deoxygenation

KW - Phospho sugar

KW - α-Hydroxyphosphonate

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U2 - 10.1016/S0008-6215(03)00235-0

DO - 10.1016/S0008-6215(03)00235-0

M3 - Article

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AN - SCOPUS:0038487613

VL - 338

SP - 1641

EP - 1650

JO - Carbohydrate Research

JF - Carbohydrate Research

SN - 0008-6215

IS - 16

ER -

Stereoselectivity in deoxygenation of 5-hydroxy-5-phosphinyl-hexofuranoses (α-hydroxyphosphonates)

Abstract

Keywords

ASJC Scopus subject areas

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