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

Institute for Education and Student Services

Research output: Contribution to journal › Article

18 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

Fingerprint

Keywords

α-Hydroxyphosphonate
Deoxygenation
Phospho sugar

ASJC Scopus subject areas

Biochemistry
Molecular Biology
Organic Chemistry

Cite this

Hanaya, T., Sugiyama, K. I., Kawamoto, H., & Yamamoto, H. (2003). Stereoselectivity in deoxygenation of 5-hydroxy-5-phosphinyl-hexofuranoses (α-hydroxyphosphonates). Carbohydrate Research, 338(16), 1641-1650. https://doi.org/10.1016/S0008-6215(03)00235-0

@article{e4eba2b336714f7fad98d1ded979056a,

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

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

year = "2003",

month = jul

day = "29",

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

language = "English",

volume = "338",

pages = "1641--1650",

journal = "Carbohydrate Research",

issn = "0008-6215",

publisher = "Elsevier BV",

number = "16",

}

TY - JOUR

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 - α-Hydroxyphosphonate

KW - Deoxygenation

KW - Phospho sugar

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

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

VL - 338

SP - 1641

EP - 1650

JO - Carbohydrate Research

JF - Carbohydrate Research

SN - 0008-6215

IS - 16

ER -

Access to Document

10.1016/S0008-6215(03)00235-0