Synthesis of 2,4-dideoxy-4-[(S)-methyl- and (R)-cyclohexylphosphinyl]-α,β-D-erythro-pentofuranoses. The first P-in-ring sugar analogues of 2-deoxy-D-ribofuranose type

Hiroshi Yamamoto; Ayashi Noguchi; Kenji Torii; Keiji Ohno; Tadashi Hanaya; Heizan Kawamoto; Saburo Inokawa

doi:10.1246/cl.1988.1575

Synthesis of 2,4-dideoxy-4-[(S)-methyl- and (R)-cyclohexylphosphinyl]-α,β-D-erythro-pentofuranoses. The first P-in-ring sugar analogues of 2-deoxy-D-ribofuranose type

Hiroshi Yamamoto, Ayashi Noguchi, Kenji Torii, Keiji Ohno, Tadashi Hanaya, Heizan Kawamoto, Saburo Inokawa

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

9 Citations (Scopus)

Abstract

Starting with 3-deoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose, methyl 2,4-dideoxy-4-[(methoxy)methyl- and cyclohexylphosphinyl]-D-glycero-pentopyranosides were prepared in a 9 step sequence (20-25% overall yield). These were converted into the title compounds, which were characterized as the 1,3,5-tri-O-acetates.

Original language	English
Pages (from-to)	1575-1576
Number of pages	2
Journal	Chemistry Letters
Volume	17
Issue number	9
DOIs	https://doi.org/10.1246/cl.1988.1575
Publication status	Published - 1988

ASJC Scopus subject areas

Chemistry(all)

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title = "Synthesis of 2,4-dideoxy-4-[(S)-methyl- and (R)-cyclohexylphosphinyl]-α,β-D-erythro-pentofuranoses. The first P-in-ring sugar analogues of 2-deoxy-D-ribofuranose type",

abstract = "Starting with 3-deoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose, methyl 2,4-dideoxy-4-[(methoxy)methyl- and cyclohexylphosphinyl]-D-glycero-pentopyranosides were prepared in a 9 step sequence (20-25% overall yield). These were converted into the title compounds, which were characterized as the 1,3,5-tri-O-acetates.",

author = "Hiroshi Yamamoto and Ayashi Noguchi and Kenji Torii and Keiji Ohno and Tadashi Hanaya and Heizan Kawamoto and Saburo Inokawa",

year = "1988",

doi = "10.1246/cl.1988.1575",

language = "English",

volume = "17",

pages = "1575--1576",

journal = "Chemistry Letters",

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publisher = "Chemical Society of Japan",

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T1 - Synthesis of 2,4-dideoxy-4-[(S)-methyl- and (R)-cyclohexylphosphinyl]-α,β-D-erythro-pentofuranoses. The first P-in-ring sugar analogues of 2-deoxy-D-ribofuranose type

AU - Yamamoto, Hiroshi

AU - Noguchi, Ayashi

AU - Torii, Kenji

AU - Ohno, Keiji

AU - Hanaya, Tadashi

AU - Kawamoto, Heizan

AU - Inokawa, Saburo

PY - 1988

Y1 - 1988

N2 - Starting with 3-deoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose, methyl 2,4-dideoxy-4-[(methoxy)methyl- and cyclohexylphosphinyl]-D-glycero-pentopyranosides were prepared in a 9 step sequence (20-25% overall yield). These were converted into the title compounds, which were characterized as the 1,3,5-tri-O-acetates.

AB - Starting with 3-deoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose, methyl 2,4-dideoxy-4-[(methoxy)methyl- and cyclohexylphosphinyl]-D-glycero-pentopyranosides were prepared in a 9 step sequence (20-25% overall yield). These were converted into the title compounds, which were characterized as the 1,3,5-tri-O-acetates.

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DO - 10.1246/cl.1988.1575

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JO - Chemistry Letters

JF - Chemistry Letters

IS - 9

ER -

Synthesis of 2,4-dideoxy-4-[(S)-methyl- and (R)-cyclohexylphosphinyl]-α,β-D-erythro-pentofuranoses. The first P-in-ring sugar analogues of 2-deoxy-D-ribofuranose type

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