Solventless synthesis of acyl phosphonamidates, precursors to masked bisphosphonates

Kerri Crossey; Marie E. Migaud

doi:10.1039/c5cc03549j

Solventless synthesis of acyl phosphonamidates, precursors to masked bisphosphonates

Kerri Crossey, Marie E. Migaud^*

^*Corresponding author for this work

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

4 Citations (Scopus)

Abstract

A series of acyl phosphonamidates, the synthetic precursors to bisphosphonates, have been readily prepared from phosphoramidite type reagents and a range of acid chlorides. These reactions were performed using solventless conditions, where purification was easily achieved using column chromatography with yields ranging from 71-90%. Furthermore, we have demonstrated that these acyl phosphonamidates could be used for the preparation of unsymmetrical bisphosphonates, which do date are scarcely reported in the literature.

Original language	English
Pages (from-to)	11088-11091
Number of pages	4
Journal	Chemical Communications
Volume	51
Issue number	55
Early online date	09 Jun 2015
DOIs	https://doi.org/10.1039/c5cc03549j
Publication status	Published - 14 Jul 2015

Keywords

ALPHA-KETOPHOSPHONATES
ANTICANCER ACTIVITY
EFFICIENT METHOD
DERIVATIVES
ESTERS
PRODRUGS
PHOSPHORODIAMIDITES
PHOSPHONATES
NUCLEOSIDE
ETIDRONATE

ASJC Scopus subject areas

General Chemistry
Catalysis
Ceramics and Composites
Electronic, Optical and Magnetic Materials
Surfaces, Coatings and Films
Materials Chemistry
Metals and Alloys

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title = "Solventless synthesis of acyl phosphonamidates, precursors to masked bisphosphonates",

abstract = "A series of acyl phosphonamidates, the synthetic precursors to bisphosphonates, have been readily prepared from phosphoramidite type reagents and a range of acid chlorides. These reactions were performed using solventless conditions, where purification was easily achieved using column chromatography with yields ranging from 71-90%. Furthermore, we have demonstrated that these acyl phosphonamidates could be used for the preparation of unsymmetrical bisphosphonates, which do date are scarcely reported in the literature.",

keywords = "ALPHA-KETOPHOSPHONATES, ANTICANCER ACTIVITY, EFFICIENT METHOD, DERIVATIVES, ESTERS, PRODRUGS, PHOSPHORODIAMIDITES, PHOSPHONATES, NUCLEOSIDE, ETIDRONATE",

author = "Kerri Crossey and Migaud, {Marie E.}",

year = "2015",

month = jul,

day = "14",

doi = "10.1039/c5cc03549j",

language = "English",

volume = "51",

pages = "11088--11091",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "55",

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TY - JOUR

T1 - Solventless synthesis of acyl phosphonamidates, precursors to masked bisphosphonates

AU - Crossey, Kerri

AU - Migaud, Marie E.

PY - 2015/7/14

Y1 - 2015/7/14

N2 - A series of acyl phosphonamidates, the synthetic precursors to bisphosphonates, have been readily prepared from phosphoramidite type reagents and a range of acid chlorides. These reactions were performed using solventless conditions, where purification was easily achieved using column chromatography with yields ranging from 71-90%. Furthermore, we have demonstrated that these acyl phosphonamidates could be used for the preparation of unsymmetrical bisphosphonates, which do date are scarcely reported in the literature.

AB - A series of acyl phosphonamidates, the synthetic precursors to bisphosphonates, have been readily prepared from phosphoramidite type reagents and a range of acid chlorides. These reactions were performed using solventless conditions, where purification was easily achieved using column chromatography with yields ranging from 71-90%. Furthermore, we have demonstrated that these acyl phosphonamidates could be used for the preparation of unsymmetrical bisphosphonates, which do date are scarcely reported in the literature.

KW - ALPHA-KETOPHOSPHONATES

KW - ANTICANCER ACTIVITY

KW - EFFICIENT METHOD

KW - DERIVATIVES

KW - ESTERS

KW - PRODRUGS

KW - PHOSPHORODIAMIDITES

KW - PHOSPHONATES

KW - NUCLEOSIDE

KW - ETIDRONATE

U2 - 10.1039/c5cc03549j

DO - 10.1039/c5cc03549j

M3 - Article

C2 - 26068798

SN - 1359-7345

VL - 51

SP - 11088

EP - 11091

JO - Chemical Communications

JF - Chemical Communications

IS - 55

ER -

Solventless synthesis of acyl phosphonamidates, precursors to masked bisphosphonates

Abstract

Keywords

ASJC Scopus subject areas

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