Expeditious convergent procedure for the preparation of bis(POC) prodrugs of new (E)-4-phosphono-but-2-en-1-yl nucleosides

Aurelien Montagu; Ugo Pradere; Vincent Roy; Steven Patrick Nolan; Luigi A. Agrofoglio

doi:10.1016/j.tet.2011.05.017

Expeditious convergent procedure for the preparation of bis(POC) prodrugs of new (E)-4-phosphono-but-2-en-1-yl nucleosides

Aurelien Montagu, Ugo Pradere, Vincent Roy, Steven Patrick Nolan, Luigi A. Agrofoglio

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

Abstract

A series of unsaturated acyclonucleoside bis(POC) prodrugs of E configuration were synthesized through an expeditious, highly efficient and stereoselective one-step procedure from corresponding bis(POC)allylphosphonate through Ru catalyzed cross-coupling metathesis reaction. The [RuCl2(PCy3)(SIPr)(Indenylidene)]
and [RuCl2(PCy3)(IMes)(benzylidene)] catalysts were employed; the unsaturated ANP were used bore C5-halovinyl uracil, C5-dihalovinyluracil or furanopyrimidine motifs. The chemical cleavage of biolabile (POC) group is a useful pathway to acid phosphonate derivatives.

Original language	English
Pages (from-to)	5319-5328
Number of pages	10
Journal	Tetrahedron
Volume	67
Early online date	12 May 2011
DOIs	https://doi.org/10.1016/j.tet.2011.05.017
Publication status	Published - 2011

Keywords

Acyclonucleoside phosphonates, Prodrug, Olefin cross metathesis

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title = "Expeditious convergent procedure for the preparation of bis(POC) prodrugs of new (E)-4-phosphono-but-2-en-1-yl nucleosides",

abstract = "A series of unsaturated acyclonucleoside bis(POC) prodrugs of E configuration were synthesized through an expeditious, highly efficient and stereoselective one-step procedure from corresponding bis(POC)allylphosphonate through Ru catalyzed cross-coupling metathesis reaction. The [RuCl2(PCy3)(SIPr)(Indenylidene)]and [RuCl2(PCy3)(IMes)(benzylidene)] catalysts were employed; the unsaturated ANP were used bore C5-halovinyl uracil, C5-dihalovinyluracil or furanopyrimidine motifs. The chemical cleavage of biolabile (POC) group is a useful pathway to acid phosphonate derivatives.",

keywords = "Acyclonucleoside phosphonates, Prodrug, Olefin cross metathesis",

author = "Aurelien Montagu and Ugo Pradere and Vincent Roy and Nolan, {Steven Patrick} and Agrofoglio, {Luigi A.}",

year = "2011",

doi = "10.1016/j.tet.2011.05.017",

language = "English",

volume = "67",

pages = "5319--5328",

journal = "Tetrahedron",

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publisher = "Elsevier",

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TY - JOUR

T1 - Expeditious convergent procedure for the preparation of bis(POC) prodrugs of new (E)-4-phosphono-but-2-en-1-yl nucleosides

AU - Montagu, Aurelien

AU - Pradere, Ugo

AU - Roy, Vincent

AU - Nolan, Steven Patrick

AU - Agrofoglio, Luigi A.

PY - 2011

Y1 - 2011

N2 - A series of unsaturated acyclonucleoside bis(POC) prodrugs of E configuration were synthesized through an expeditious, highly efficient and stereoselective one-step procedure from corresponding bis(POC)allylphosphonate through Ru catalyzed cross-coupling metathesis reaction. The [RuCl2(PCy3)(SIPr)(Indenylidene)]and [RuCl2(PCy3)(IMes)(benzylidene)] catalysts were employed; the unsaturated ANP were used bore C5-halovinyl uracil, C5-dihalovinyluracil or furanopyrimidine motifs. The chemical cleavage of biolabile (POC) group is a useful pathway to acid phosphonate derivatives.

AB - A series of unsaturated acyclonucleoside bis(POC) prodrugs of E configuration were synthesized through an expeditious, highly efficient and stereoselective one-step procedure from corresponding bis(POC)allylphosphonate through Ru catalyzed cross-coupling metathesis reaction. The [RuCl2(PCy3)(SIPr)(Indenylidene)]and [RuCl2(PCy3)(IMes)(benzylidene)] catalysts were employed; the unsaturated ANP were used bore C5-halovinyl uracil, C5-dihalovinyluracil or furanopyrimidine motifs. The chemical cleavage of biolabile (POC) group is a useful pathway to acid phosphonate derivatives.

KW - Acyclonucleoside phosphonates, Prodrug, Olefin cross metathesis

U2 - 10.1016/j.tet.2011.05.017

DO - 10.1016/j.tet.2011.05.017

M3 - Article

SN - 0040-4020

VL - 67

SP - 5319

EP - 5328

JO - Tetrahedron

JF - Tetrahedron

ER -

Expeditious convergent procedure for the preparation of bis(POC) prodrugs of new (E)-4-phosphono-but-2-en-1-yl nucleosides

Abstract

Keywords

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