Click Azide-Alkyne Cycloaddition for the Synthesis of D-(-)-1,4-Disubstituted Triazolo-Carbanucleosides

Julie Broggi; Hiroki Kumamoto; Sabine Berteina-Raboin; Steven Patrick Nolan; Luigi A. Agrofoglio

doi:10.1002/ejoc.200801124

Click Azide-Alkyne Cycloaddition for the Synthesis of D-(-)-1,4-Disubstituted Triazolo-Carbanucleosides

Julie Broggi, Hiroki Kumamoto, Sabine Berteina-Raboin, Steven Patrick Nolan, Luigi A. Agrofoglio

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

Abstract

A revisited and improved synthesis of an optically active azido-carbanucleoside is reported. This azido precursor is used in the successful and versatile synthesis of enantiomerically pure D-(-)-1,4-disubstituted 1,2,3-triazolo-carbanucleosides via copper(I)-catalyzed and microwave-assisted Huisgen 1,3-dipolar cycloaddition. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

Original language	English
Pages (from-to)	1880-1888
Number of pages	9
Journal	European Journal of Organic Chemistry
Issue number	12
DOIs	https://doi.org/10.1002/ejoc.200801124
Publication status	Published - Apr 2009

Keywords

Nucleosides
Carbanucleosides
Antiviral agents
Olefin metathesis
Huisgen cycloaddition
Ribavirin
Poxvirus
RING-CLOSING METATHESIS
CONJUGATE ADDITION-REACTION
REVERSED CYCLONUCLEOSIDE ANALOGS
S-ADENOSYLHOMOCYSTEINE HYDROLASE
L-CYCLOPENTENONE DERIVATIVES
ORTHOPOX VIRUSES SMALLPOX
CARBOCYCLIC NUCLEOSIDES
ANTIVIRAL ACTIVITY
PRACTICAL SYNTHESIS
ENANTIOSELECTIVE SYNTHESIS

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10.1002/ejoc.200801124

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title = "Click Azide-Alkyne Cycloaddition for the Synthesis of D-(-)-1,4-Disubstituted Triazolo-Carbanucleosides",

abstract = "A revisited and improved synthesis of an optically active azido-carbanucleoside is reported. This azido precursor is used in the successful and versatile synthesis of enantiomerically pure D-(-)-1,4-disubstituted 1,2,3-triazolo-carbanucleosides via copper(I)-catalyzed and microwave-assisted Huisgen 1,3-dipolar cycloaddition. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)",

keywords = "Nucleosides, Carbanucleosides, Antiviral agents, Olefin metathesis, Huisgen cycloaddition, Ribavirin, Poxvirus, RING-CLOSING METATHESIS, CONJUGATE ADDITION-REACTION, REVERSED CYCLONUCLEOSIDE ANALOGS, S-ADENOSYLHOMOCYSTEINE HYDROLASE, L-CYCLOPENTENONE DERIVATIVES, ORTHOPOX VIRUSES SMALLPOX, CARBOCYCLIC NUCLEOSIDES, ANTIVIRAL ACTIVITY, PRACTICAL SYNTHESIS, ENANTIOSELECTIVE SYNTHESIS",

author = "Julie Broggi and Hiroki Kumamoto and Sabine Berteina-Raboin and Nolan, {Steven Patrick} and Agrofoglio, {Luigi A.}",

year = "2009",

month = apr,

doi = "10.1002/ejoc.200801124",

language = "English",

pages = "1880--1888",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH, Weinheim",

number = "12",

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T1 - Click Azide-Alkyne Cycloaddition for the Synthesis of D-(-)-1,4-Disubstituted Triazolo-Carbanucleosides

AU - Broggi, Julie

AU - Kumamoto, Hiroki

AU - Berteina-Raboin, Sabine

AU - Nolan, Steven Patrick

AU - Agrofoglio, Luigi A.

PY - 2009/4

Y1 - 2009/4

N2 - A revisited and improved synthesis of an optically active azido-carbanucleoside is reported. This azido precursor is used in the successful and versatile synthesis of enantiomerically pure D-(-)-1,4-disubstituted 1,2,3-triazolo-carbanucleosides via copper(I)-catalyzed and microwave-assisted Huisgen 1,3-dipolar cycloaddition. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

AB - A revisited and improved synthesis of an optically active azido-carbanucleoside is reported. This azido precursor is used in the successful and versatile synthesis of enantiomerically pure D-(-)-1,4-disubstituted 1,2,3-triazolo-carbanucleosides via copper(I)-catalyzed and microwave-assisted Huisgen 1,3-dipolar cycloaddition. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

KW - Nucleosides

KW - Carbanucleosides

KW - Antiviral agents

KW - Olefin metathesis

KW - Huisgen cycloaddition

KW - Ribavirin

KW - Poxvirus

KW - RING-CLOSING METATHESIS

KW - CONJUGATE ADDITION-REACTION

KW - REVERSED CYCLONUCLEOSIDE ANALOGS

KW - S-ADENOSYLHOMOCYSTEINE HYDROLASE

KW - L-CYCLOPENTENONE DERIVATIVES

KW - ORTHOPOX VIRUSES SMALLPOX

KW - CARBOCYCLIC NUCLEOSIDES

KW - ANTIVIRAL ACTIVITY

KW - PRACTICAL SYNTHESIS

KW - ENANTIOSELECTIVE SYNTHESIS

UR - http://www.scopus.com/inward/record.url?scp=63849232743&partnerID=8YFLogxK

U2 - 10.1002/ejoc.200801124

DO - 10.1002/ejoc.200801124

M3 - Article

SN - 1434-193X

SP - 1880

EP - 1888

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 12

ER -

Click Azide-Alkyne Cycloaddition for the Synthesis of D-(-)-1,4-Disubstituted Triazolo-Carbanucleosides

Abstract

Keywords

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