Synthesis of 5-deoxy-5-hydroxyphosphinyl-d-mannopyranoses

Tadashi Hanaya; Kunihiro Hirose; Hiroshi Yamamoto

doi:10.3987/com-93-6483

Synthesis of 5-deoxy-5-hydroxyphosphinyl-d-mannopyranoses

Tadashi Hanaya, Kunihiro Hirose, Hiroshi Yamamoto

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8 Citations (Scopus)

Abstract

The title sugar analogues (13) were synthesized by starting with known methyl (E)-5,6-dideoxy-2,3-O-isopropylidene-6-nitro-α-d-lyxo-hex-5-enofuranoside (5a) in six steps through the key intermediate, methyl 5-deoxy-5-dimethoxy-phosphinyl-2,3-O-isopropylidene-α-d-mannofuranoside 8a). The products (13) were converted into the corresponding penta-O-acetyl-5-methoxyphosphinyl derivatives (14), whose structures and conformations (mostly ⁴C₁) were established by spectroscopy.

Original language	English
Pages (from-to)	2557-2564
Number of pages	8
Journal	Heterocycles
Volume	36
Issue number	11
DOIs	https://doi.org/10.3987/com-93-6483
Publication status	Published - Nov 1 1993

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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title = "Synthesis of 5-deoxy-5-hydroxyphosphinyl-d-mannopyranoses",

abstract = "The title sugar analogues (13) were synthesized by starting with known methyl (E)-5,6-dideoxy-2,3-O-isopropylidene-6-nitro-α-d-lyxo-hex-5-enofuranoside (5a) in six steps through the key intermediate, methyl 5-deoxy-5-dimethoxy-phosphinyl-2,3-O-isopropylidene-α-d-mannofuranoside 8a). The products (13) were converted into the corresponding penta-O-acetyl-5-methoxyphosphinyl derivatives (14), whose structures and conformations (mostly 4C1) were established by spectroscopy.",

author = "Tadashi Hanaya and Kunihiro Hirose and Hiroshi Yamamoto",

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doi = "10.3987/com-93-6483",

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T1 - Synthesis of 5-deoxy-5-hydroxyphosphinyl-d-mannopyranoses

AU - Hanaya, Tadashi

AU - Hirose, Kunihiro

AU - Yamamoto, Hiroshi

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N2 - The title sugar analogues (13) were synthesized by starting with known methyl (E)-5,6-dideoxy-2,3-O-isopropylidene-6-nitro-α-d-lyxo-hex-5-enofuranoside (5a) in six steps through the key intermediate, methyl 5-deoxy-5-dimethoxy-phosphinyl-2,3-O-isopropylidene-α-d-mannofuranoside 8a). The products (13) were converted into the corresponding penta-O-acetyl-5-methoxyphosphinyl derivatives (14), whose structures and conformations (mostly 4C1) were established by spectroscopy.

AB - The title sugar analogues (13) were synthesized by starting with known methyl (E)-5,6-dideoxy-2,3-O-isopropylidene-6-nitro-α-d-lyxo-hex-5-enofuranoside (5a) in six steps through the key intermediate, methyl 5-deoxy-5-dimethoxy-phosphinyl-2,3-O-isopropylidene-α-d-mannofuranoside 8a). The products (13) were converted into the corresponding penta-O-acetyl-5-methoxyphosphinyl derivatives (14), whose structures and conformations (mostly 4C1) were established by spectroscopy.

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