Novel efficient synthesis and structural analysis of furanose-type phosphono sugars

Mitsuji Yamashita; Akihiro Yabui; Tatsuo Oshikawa; Tadashi Hanaya; Hiroshi Yamamoto

doi:10.3987/COM-93-6665

Novel efficient synthesis and structural analysis of furanose-type phosphono sugars

Mitsuji Yamashita, Akihiro Yabui, Tatsuo Oshikawa, Tadashi Hanaya, Hiroshi Yamamoto

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

5 Citations (Scopus)

Abstract

Reaction of 2-benzyloxymethyl-1-methoxy-3-phospholene 1-oxide with mCPBA afforded 3,4-epoxyphospholane derivatives, whose isomerized allylic alcohols were cis-dihydroxylated by osmium(VIII) oxide-catalyzed oxidation to give ribo-, arabino-, xylo-, and lyxofuranose-type phosphono sugars. The nmr data suggest a twist conformation.

Original language	English
Pages (from-to)	1449-1452
Number of pages	4
Journal	Heterocycles
Volume	38
Issue number	7
DOIs	https://doi.org/10.3987/COM-93-6665
Publication status	Published - Jul 1 1994

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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abstract = "Reaction of 2-benzyloxymethyl-1-methoxy-3-phospholene 1-oxide with mCPBA afforded 3,4-epoxyphospholane derivatives, whose isomerized allylic alcohols were cis-dihydroxylated by osmium(VIII) oxide-catalyzed oxidation to give ribo-, arabino-, xylo-, and lyxofuranose-type phosphono sugars. The nmr data suggest a twist conformation.",

author = "Mitsuji Yamashita and Akihiro Yabui and Tatsuo Oshikawa and Tadashi Hanaya and Hiroshi Yamamoto",

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T1 - Novel efficient synthesis and structural analysis of furanose-type phosphono sugars

AU - Yamashita, Mitsuji

AU - Yabui, Akihiro

AU - Oshikawa, Tatsuo

AU - Hanaya, Tadashi

AU - Yamamoto, Hiroshi

PY - 1994/7/1

Y1 - 1994/7/1

N2 - Reaction of 2-benzyloxymethyl-1-methoxy-3-phospholene 1-oxide with mCPBA afforded 3,4-epoxyphospholane derivatives, whose isomerized allylic alcohols were cis-dihydroxylated by osmium(VIII) oxide-catalyzed oxidation to give ribo-, arabino-, xylo-, and lyxofuranose-type phosphono sugars. The nmr data suggest a twist conformation.

AB - Reaction of 2-benzyloxymethyl-1-methoxy-3-phospholene 1-oxide with mCPBA afforded 3,4-epoxyphospholane derivatives, whose isomerized allylic alcohols were cis-dihydroxylated by osmium(VIII) oxide-catalyzed oxidation to give ribo-, arabino-, xylo-, and lyxofuranose-type phosphono sugars. The nmr data suggest a twist conformation.

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JO - Heterocycles

JF - Heterocycles

IS - 7

ER -

Novel efficient synthesis and structural analysis of furanose-type phosphono sugars

Abstract

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