Synthesis and structural analysis of 6-deoxy-6-hydroxyphosphinyl-d- fructopyranose derivatives

Tadashi Hanaya; Kumiko Imai; Yurij V. Prikhod'Ko; Hiroshi Yamamoto

doi:10.1016/j.carres.2004.10.020

Synthesis and structural analysis of 6-deoxy-6-hydroxyphosphinyl-d- fructopyranose derivatives

Tadashi Hanaya, Kumiko Imai, Yurij V. Prikhod'Ko, Hiroshi Yamamoto

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

4 Citations (Scopus)

Abstract

3,4-Di-O-benzyl-6-deoxy-6-diethoxyphosphinyl-1,2-O-isopropylidene-β-d- fructofuranose (13) was prepared from the known 1,2-O-isopropylidene-6-O-tosyl- β-d-fructofuranose in five steps. Reduction of 13 with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by the action of hydrochloric acid and then hydrogen peroxide, afforded the 6-deoxy-6-hydroxyphosphinyl-d- fructopyranose derivative. This was converted into the 1,2,3,4,5-penta-O-acetyl- 6-deoxy-6-methoxyphosphinyl-d-fructopyranoses, whose structure and conformation were established by ¹H NMR spectroscopy.

Original language	English
Pages (from-to)	31-37
Number of pages	7
Journal	Carbohydrate Research
Volume	340
Issue number	1
DOIs	https://doi.org/10.1016/j.carres.2004.10.020
Publication status	Published - Jan 17 2005

Keywords

6-Deoxy-6-phosphinyl-d-fructopyranose
Acetyl migration
Conformational analysis
Hydroxyphosphinyl group
Phospho sugar

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Organic Chemistry

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10.1016/j.carres.2004.10.020

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title = "Synthesis and structural analysis of 6-deoxy-6-hydroxyphosphinyl-d- fructopyranose derivatives",

abstract = "3,4-Di-O-benzyl-6-deoxy-6-diethoxyphosphinyl-1,2-O-isopropylidene-β-d- fructofuranose (13) was prepared from the known 1,2-O-isopropylidene-6-O-tosyl- β-d-fructofuranose in five steps. Reduction of 13 with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by the action of hydrochloric acid and then hydrogen peroxide, afforded the 6-deoxy-6-hydroxyphosphinyl-d- fructopyranose derivative. This was converted into the 1,2,3,4,5-penta-O-acetyl- 6-deoxy-6-methoxyphosphinyl-d-fructopyranoses, whose structure and conformation were established by 1H NMR spectroscopy.",

keywords = "6-Deoxy-6-phosphinyl-d-fructopyranose, Acetyl migration, Conformational analysis, Hydroxyphosphinyl group, Phospho sugar",

author = "Tadashi Hanaya and Kumiko Imai and Prikhod'Ko, {Yurij V.} and Hiroshi Yamamoto",

year = "2005",

month = jan,

day = "17",

doi = "10.1016/j.carres.2004.10.020",

language = "English",

volume = "340",

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journal = "Carbohydrate Research",

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T1 - Synthesis and structural analysis of 6-deoxy-6-hydroxyphosphinyl-d- fructopyranose derivatives

AU - Hanaya, Tadashi

AU - Imai, Kumiko

AU - Prikhod'Ko, Yurij V.

AU - Yamamoto, Hiroshi

PY - 2005/1/17

Y1 - 2005/1/17

N2 - 3,4-Di-O-benzyl-6-deoxy-6-diethoxyphosphinyl-1,2-O-isopropylidene-β-d- fructofuranose (13) was prepared from the known 1,2-O-isopropylidene-6-O-tosyl- β-d-fructofuranose in five steps. Reduction of 13 with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by the action of hydrochloric acid and then hydrogen peroxide, afforded the 6-deoxy-6-hydroxyphosphinyl-d- fructopyranose derivative. This was converted into the 1,2,3,4,5-penta-O-acetyl- 6-deoxy-6-methoxyphosphinyl-d-fructopyranoses, whose structure and conformation were established by 1H NMR spectroscopy.

AB - 3,4-Di-O-benzyl-6-deoxy-6-diethoxyphosphinyl-1,2-O-isopropylidene-β-d- fructofuranose (13) was prepared from the known 1,2-O-isopropylidene-6-O-tosyl- β-d-fructofuranose in five steps. Reduction of 13 with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by the action of hydrochloric acid and then hydrogen peroxide, afforded the 6-deoxy-6-hydroxyphosphinyl-d- fructopyranose derivative. This was converted into the 1,2,3,4,5-penta-O-acetyl- 6-deoxy-6-methoxyphosphinyl-d-fructopyranoses, whose structure and conformation were established by 1H NMR spectroscopy.

KW - 6-Deoxy-6-phosphinyl-d-fructopyranose

KW - Acetyl migration

KW - Conformational analysis

KW - Hydroxyphosphinyl group

KW - Phospho sugar

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ER -

Synthesis and structural analysis of 6-deoxy-6-hydroxyphosphinyl-d- fructopyranose derivatives

Abstract

Keywords

ASJC Scopus subject areas

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