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

研究成果 › 査読

20 被引用数 (Scopus)

抄録

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.

本文言語	English
ページ（範囲）	1641-1650
ページ数	10
ジャーナル	Carbohydrate Research
巻	338
号	16
DOI	https://doi.org/10.1016/S0008-6215(03)00235-0
出版ステータス	Published - 7月 29 2003

ASJC Scopus subject areas

分析化学
生化学
有機化学

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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.",

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

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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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UR - http://www.scopus.com/inward/citedby.url?scp=0038487613&partnerID=8YFLogxK

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

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

M3 - Article

C2 - 12873420

AN - SCOPUS:0038487613

SN - 0008-6215

VL - 338

SP - 1641

EP - 1650

JO - Carbohydrate Research

JF - Carbohydrate Research

IS - 16

ER -

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

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