An efficient, one-pot synthesis of fosfomycin dialkyl esters from (R)-2-tosyloxypropanal

Tadashi Hanaya; Yuichi Nakamura; Hiroshi Yamamoto

doi:10.3987/com-07-s(w)45

An efficient, one-pot synthesis of fosfomycin dialkyl esters from (R)-2-tosyloxypropanal

Tadashi Hanaya, Yuichi Nakamura, Hiroshi Yamamoto

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

2 Citations (Scopus)

Abstract

(R)-2-Tosyloxypropanal (4) was prepared from D-mannitol in a 7-step sequence (51% overall yield). Addition of dialkyl phosphonates to 4 in the presence of titanium isopropoxide and the subsequent treatment with DBU stereoselectively afforded, in one-pot, fosfomycin dimethyl (5a) and dibenzyl (5b) esters both in 58% isolated yield.

Original language	English
Pages (from-to)	983-989
Number of pages	7
Journal	Heterocycles
Volume	74
Issue number	C
DOIs	https://doi.org/10.3987/com-07-s(w)45
Publication status	Published - Dec 31 2007

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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abstract = "(R)-2-Tosyloxypropanal (4) was prepared from D-mannitol in a 7-step sequence (51% overall yield). Addition of dialkyl phosphonates to 4 in the presence of titanium isopropoxide and the subsequent treatment with DBU stereoselectively afforded, in one-pot, fosfomycin dimethyl (5a) and dibenzyl (5b) esters both in 58% isolated yield.",

author = "Tadashi Hanaya and Yuichi Nakamura and Hiroshi Yamamoto",

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T1 - An efficient, one-pot synthesis of fosfomycin dialkyl esters from (R)-2-tosyloxypropanal

AU - Hanaya, Tadashi

AU - Nakamura, Yuichi

AU - Yamamoto, Hiroshi

PY - 2007/12/31

Y1 - 2007/12/31

N2 - (R)-2-Tosyloxypropanal (4) was prepared from D-mannitol in a 7-step sequence (51% overall yield). Addition of dialkyl phosphonates to 4 in the presence of titanium isopropoxide and the subsequent treatment with DBU stereoselectively afforded, in one-pot, fosfomycin dimethyl (5a) and dibenzyl (5b) esters both in 58% isolated yield.

AB - (R)-2-Tosyloxypropanal (4) was prepared from D-mannitol in a 7-step sequence (51% overall yield). Addition of dialkyl phosphonates to 4 in the presence of titanium isopropoxide and the subsequent treatment with DBU stereoselectively afforded, in one-pot, fosfomycin dimethyl (5a) and dibenzyl (5b) esters both in 58% isolated yield.

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JO - Heterocycles

JF - Heterocycles

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ER -

An efficient, one-pot synthesis of fosfomycin dialkyl esters from (R)-2-tosyloxypropanal

Abstract

ASJC Scopus subject areas

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