Synthesis of 5-deoxy-5-phosphinyl-D-galactopyranose derivatives: New phospha-sugar analogs of D-galactose

Tadashi Hanaya; Ken Ichi Sugiyama; Yasushi Fujii; Akihito Akamatsu; Hiroshi Yamamoto

doi:10.3987/com-01-9235

Synthesis of 5-deoxy-5-phosphinyl-D-galactopyranose derivatives: New phospha-sugar analogs of D-galactose

Tadashi Hanaya, Ken Ichi Sugiyama, Yasushi Fujii, Akihito Akamatsu, Hiroshi Yamamoto

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

9 Citations (Scopus)

Abstract

The addition reaction of dimethyl phosphonate to 3,6-di-O-benzyl-1,2-O-isopropylidene-α-L-arabino-hexofuranos-5-ulose (11), followed by deoxygenation of 5-hydroxyl group, provided 5-deoxy-5-dimethoxyphosphinyl-D-galactofuranose derivative (13a). Reduction of 13a with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by the action of hydrochloric acid and then hydrogen peroxide, afforded the first D-galactopyranose analog (15) having a phosphinyl group in the hemiacetal ring. This was converted into the 1,2,4-tri-O-acetyl-5-methoxyphosphinyl derivatives (16), whose structure and conformation were established by ¹H-NMR spectroscopy.

Original language	English
Pages (from-to)	1301-1309
Number of pages	9
Journal	Heterocycles
Volume	55
Issue number	7
DOIs	https://doi.org/10.3987/com-01-9235
Publication status	Published - Jul 1 2001

Keywords

C-P bond
Deoxygenation
Heterosugar
Hexofuranos-5-ulose
Phosphorinane

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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title = "Synthesis of 5-deoxy-5-phosphinyl-D-galactopyranose derivatives: New phospha-sugar analogs of D-galactose",

abstract = "The addition reaction of dimethyl phosphonate to 3,6-di-O-benzyl-1,2-O-isopropylidene-α-L-arabino-hexofuranos-5-ulose (11), followed by deoxygenation of 5-hydroxyl group, provided 5-deoxy-5-dimethoxyphosphinyl-D-galactofuranose derivative (13a). Reduction of 13a with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by the action of hydrochloric acid and then hydrogen peroxide, afforded the first D-galactopyranose analog (15) having a phosphinyl group in the hemiacetal ring. This was converted into the 1,2,4-tri-O-acetyl-5-methoxyphosphinyl derivatives (16), whose structure and conformation were established by 1H-NMR spectroscopy.",

keywords = "C-P bond, Deoxygenation, Heterosugar, Hexofuranos-5-ulose, Phosphorinane",

author = "Tadashi Hanaya and Sugiyama, {Ken Ichi} and Yasushi Fujii and Akihito Akamatsu and Hiroshi Yamamoto",

year = "2001",

month = jul,

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doi = "10.3987/com-01-9235",

language = "English",

volume = "55",

pages = "1301--1309",

journal = "Heterocycles",

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T1 - Synthesis of 5-deoxy-5-phosphinyl-D-galactopyranose derivatives

T2 - New phospha-sugar analogs of D-galactose

AU - Hanaya, Tadashi

AU - Sugiyama, Ken Ichi

AU - Fujii, Yasushi

AU - Akamatsu, Akihito

AU - Yamamoto, Hiroshi

PY - 2001/7/1

Y1 - 2001/7/1

N2 - The addition reaction of dimethyl phosphonate to 3,6-di-O-benzyl-1,2-O-isopropylidene-α-L-arabino-hexofuranos-5-ulose (11), followed by deoxygenation of 5-hydroxyl group, provided 5-deoxy-5-dimethoxyphosphinyl-D-galactofuranose derivative (13a). Reduction of 13a with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by the action of hydrochloric acid and then hydrogen peroxide, afforded the first D-galactopyranose analog (15) having a phosphinyl group in the hemiacetal ring. This was converted into the 1,2,4-tri-O-acetyl-5-methoxyphosphinyl derivatives (16), whose structure and conformation were established by 1H-NMR spectroscopy.

AB - The addition reaction of dimethyl phosphonate to 3,6-di-O-benzyl-1,2-O-isopropylidene-α-L-arabino-hexofuranos-5-ulose (11), followed by deoxygenation of 5-hydroxyl group, provided 5-deoxy-5-dimethoxyphosphinyl-D-galactofuranose derivative (13a). Reduction of 13a with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by the action of hydrochloric acid and then hydrogen peroxide, afforded the first D-galactopyranose analog (15) having a phosphinyl group in the hemiacetal ring. This was converted into the 1,2,4-tri-O-acetyl-5-methoxyphosphinyl derivatives (16), whose structure and conformation were established by 1H-NMR spectroscopy.

KW - C-P bond

KW - Deoxygenation

KW - Heterosugar

KW - Hexofuranos-5-ulose

KW - Phosphorinane

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JO - Heterocycles

JF - Heterocycles

IS - 7

ER -

Synthesis of 5-deoxy-5-phosphinyl-D-galactopyranose derivatives: New phospha-sugar analogs of D-galactose

Abstract

Keywords

ASJC Scopus subject areas

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