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7057-48-9,MFCD00040965
Catalog No.:AA005HOK

7057-48-9 | 2',3'-Dideoxy-2',3'-didehydroadenosine

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1mg
95%
in stock  
$6.00   $4.00
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25mg
95%
in stock  
$42.00   $29.00
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100mg
95%
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$117.00   $82.00
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250mg
95%
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$156.00   $109.00
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500mg
95%
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$259.00   $182.00
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1g
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$388.00   $272.00
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5g
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$1,171.00   $820.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA005HOK
Chemical Name:
2',3'-Dideoxy-2',3'-didehydroadenosine
CAS Number:
7057-48-9
Molecular Formula:
C10H11N5O2
Molecular Weight:
233.2266
MDL Number:
MFCD00040965
SMILES:
OC[C@@H]1C=C[C@@H](O1)n1cnc2c1ncnc2N
Properties
Properties
 
Form:
Solid  
MP:
187-189°C  
Storage:
Keep in dry area;2-8℃;  

Computed Properties
 
Complexity:
313  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Heavy Atom Count:
17  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
2  
XLogP3:
-0.4  

Downstream Synthesis Route

[1]Robins,MorrisJ.;Hansske,Fritz;Low,NicholasH.;Park,JaIn[TetrahedronLetters,1984,vol.25,#4,p.367-370]

[2]Robins,MorrisJ.;Wilson,John,S.;Madej,Danuta;Low,NicholasH.;Hansske,Fritz;Wnuk,StanislawF.[JournalofOrganicChemistry,1995,vol.60,#24,p.7902-7908]

[3]Chu;Bhadti;Doboszewski;Gu;Kosugi;Pullaiah;VanRoey[JournalofOrganicChemistry,1989,vol.54,#9,p.2217-2225]

[4]Mansuri;StarrettJr.;Wos;Tortolani;Brodfuehrer;Howell;Martin[JournalofOrganicChemistry,1989,vol.54,#20,p.4780-4785]

7057-48-9   
<2',3',8-3H3>-2',3'-dideoxyadenosine 

[1]Sidorov,G.V.;Myasoedov,N.F.[RussianJournalofBioorganicChemistry,1993,vol.19,#12,p.727-730][BioorganicheskayaKhimiya,1993,vol.19,#12,p.1215-1219]

[2]Sidorov;Myasoedov;Yasko[Journaloflabelledcompoundsandradiopharmaceuticals,1994,vol.34,#4,p.339-351]

[3]Sidorov;Myasoedov;Yasko[Journaloflabelledcompoundsandradiopharmaceuticals,1994,vol.34,#4,p.339-351]

[1]Kai,Kenji;Fujii,Hiroki;Ikenaka,Rui;Akagawa,Mitsugu;Hayashi,Hideo[ChemicalCommunications,2014,vol.50,#62,p.8586-8589]

[2]Chu;Bhadti;Doboszewski;Gu;Kosugi;Pullaiah;VanRoey[JournalofOrganicChemistry,1989,vol.54,#9,p.2217-2225]

[3]Robins,MorrisJ.;Wnuk,StanislawF.;Hernández-Thirring,AmeliaE.;Samano,MirnaC.[JournaloftheAmericanChemicalSociety,1996,vol.118,#46,p.11341-11348]

[1]Dorland;Serafinowski[Synthesis,1992,#5,p.477-481]

[1]Talekar;Coe;Walker[Synthesis,1993,#3,p.303-306]

Literature

Title: [Conformational capacity of 2',3'-didehydro-2',3'-dideoxyadenosine as a key to understanding its biological activity: results of quantum chemical modelling].

Journal: Ukrains'kyi biokhimichnyi zhurnal (1999 ) 20110101

Title: Synthesis and antiviral evaluation of thieno[3,4-d]pyrimidine C-nucleoside analogues of 2',3'-dideoxy- and 2',3'-dideoxy-2',3'-didehydro-adenosine and -inosine.

Journal: Bioorganic & medicinal chemistry 20090315

Title: Effects of two novel nucleoside analogues on different hepatitis B virus promoters.

Journal: World journal of gastroenterology 20080328

Title: Efficacies of beta-L-D4A against Hepatitis B virus in 2.2.15 cells.

Journal: World journal of gastroenterology 20080227

Title: Inhibition of reverse transcriptase activity of hepatitis B virus polymerase by β-l-D4A-TP.

Journal: Acta virologica 20080101

Title: Effect and mechanism of beta-L-D4A on DNA polymerase alpha.

Journal: World journal of gastroenterology 20071214

Title: [Isosteric triphosphonate analogues of dNTP: synthesis and substrate properties toward various DNA polymerases].

Journal: Bioorganicheskaia khimiia 20070101

Title: Synthesis and conformational analysis of new cyclobutane-fused nucleosides.

Journal: Organic letters 20060202

Title: [Synthesis of a novel L-nucleoside, beta-L-D4A and its inhibition on the replication of hepatitis B virus in vitro].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20050901

Title: Synthesis, structure-activity relationships, and drug resistance of beta-d-3'-fluoro-2',3'-unsaturated nucleosides as anti-HIV Agents.

Journal: Journal of medicinal chemistry 20040617

Title: Inhibition of hepatitis B virus by a novel L-nucleoside, beta-L-D4A and related analogues.

Journal: World journal of gastroenterology 20030815

Title: [Inhibition of the replication of hepatitis B virus in vitro by a novel nucleoside analogue (beta-L-D4A)].

Journal: Zhonghua gan zang bing za zhi = Zhonghua ganzangbing zazhi = Chinese journal of hepatology 20030701

Title: [Effect and mechanism of beta-L-D4A (a novel nucleoside analog) against hepatitis B virus].

Journal: Zhonghua gan zang bing za zhi = Zhonghua ganzangbing zazhi = Chinese journal of hepatology 20030501

Title: Synthesis and studies of 3'-C-trifluoromethyl nucleoside analogues bearing adenine or cytosine as the base.

Journal: Bioorganic & medicinal chemistry 20021001

Title: Stereoselective synthesis of a novel carbocyclic nucleoside.

Journal: The Journal of organic chemistry 20011102

Title: Activities of masked 2',3'-dideoxynucleoside monophosphate derivatives against human immunodeficiency virus in resting macrophages.

Journal: Antimicrobial agents and chemotherapy 20000101

Title: cycloSal-Pronucleotides of 2',3'-dideoxyadenosine and 2', 3'-dideoxy-2',3'-didehydroadenosine: synthesis and antiviral evaluation of a highly efficient nucleotide delivery system.

Journal: Journal of medicinal chemistry 19990506

Title: Conversion of 2',3'-dideoxyadenosine (ddA) and 2',3'-didehydro-2',3'-dideoxyadenosine (d4A) to their corresponding aryloxyphosphoramidate derivatives markedly potentiates their activity against human immunodeficiency virus and hepatitis B virus.

Journal: FEBS letters 19970630

Title: Potential prodrug derivatives of 2',3'-didehydro-2',3'-dideoxynucleosides. Preparations and antiviral activities.

Journal: Journal of medicinal chemistry 19920724

Title: Nucleic acid related compounds. 57. Synthesis, x-ray crystal structure, lipophilic partition properties, and antiretroviral activities of anomeric 3'-azido-2',3'-dideoxy-2,6-diaminopurine ribosides.

Journal: Journal of medicinal chemistry 19890801

Title: Comparative activity of 2',3'-saturated and unsaturated pyrimidine and purine nucleosides against human immunodeficiency virus type 1 in peripheral blood mononuclear cells.

Journal: Biochemical pharmacology 19881001

Title: Investigations on the anti-HIV activity of 2',3'-dideoxyadenosine analogues with modifications in either the pentose or purine moiety. Potent and selective anti-HIV activity of 2,6-diaminopurine 2',3'-dideoxyriboside.

Journal: Biochemical pharmacology 19880401

Title: Synthesis and anti-HIV activity of various 2'- and 3'-substituted 2',3'-dideoxyadenosines: a structure-activity analysis.

Journal: Journal of medicinal chemistry 19871101

Title: 3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.

Journal: Journal of medicinal chemistry 19870801

Title: The anti-HTLV-III (anti-HIV) and cytotoxic activity of 2',3'-didehydro-2',3'-dideoxyribonucleosides: a comparison with their parental 2',3'-dideoxyribonucleosides.

Journal: Molecular pharmacology 19870701

Title: The 2',3'-dideoxyriboside of 2,6-diaminopurine selectively inhibits human immunodeficiency virus (HIV) replication in vitro.

Journal: Biochemical and biophysical research communications 19870529

Title: Both 2',3'-dideoxythymidine and its 2',3'-unsaturated derivative (2',3'-dideoxythymidinene) are potent and selective inhibitors of human immunodeficiency virus replication in vitro.

Journal: Biochemical and biophysical research communications 19870115

Title: Ponomareva AG, et al. Structural and energetic properties of the potential HIV-1 reverse transcriptase inhibitors d4A and d4G: a comprehensive theoretical investigation. J Biomol Struct Dyn. 2014;32(5):730-40.

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