Home Other Building Blocks 3736-77-4
3736-77-4,MFCD00004945
Catalog No.:AA0039IV

3736-77-4 | 2,2'-Anhydro-1(B-D-arabinofuranosyl)uracil

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100mg
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$6.00   $4.00
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5g
98%
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$11.00   $8.00
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25g
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500g
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  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA0039IV
Chemical Name:
2,2'-Anhydro-1(B-D-arabinofuranosyl)uracil
CAS Number:
3736-77-4
Molecular Formula:
C9H10N2O5
Molecular Weight:
226.1861
MDL Number:
MFCD00004945
SMILES:
OC[C@H]1O[C@@H]2[C@H]([C@@H]1O)Oc1n2ccc(=O)n1
Properties
Computed Properties
 
Complexity:
393  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Heavy Atom Count:
16  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
1  
XLogP3:
-2.5  

Upstream Synthesis Route

[1]JournaloftheAmericanChemicalSociety,1995,vol.117,#10,p.2945-2946

[1]ChemicalandPharmaceuticalBulletin,1994,vol.42,#3,p.595-598

[1]BioorganicandMedicinalChemistry,2013,vol.21,#20,p.6171-6180

Downstream Synthesis Route

[1]JournaloftheChineseChemicalSociety,2007,vol.54,p.563-568

[2]Patent:US2014/66614,2014,A1.Locationinpatent:Paragraph0018-0019

[3]Patent:EP1992632,2008,A1.Locationinpatent:Page/Pagecolumn7-8

[4]JournalfurpraktischeChemie(Leipzig1954),1983,vol.325,p.387-392

[5]MagneticResonanceinChemistry,1985,vol.23,p.885-894

[6]JournaloftheChemicalSociety,1956,p.2388,2392    JournaloftheChemicalSociety,1958,p.3028,3032

[7]JournaloftheChemicalSociety.PerkintransactionsI,1982,p.1171-1176

[8]Tetrahedron,1993,vol.49,p.10089-10098

[9]BioorganicandMedicinalChemistryLetters,2003,vol.13,p.2441-2443

[10]Patent:WO2020/72991,2020,A1.Locationinpatent:Page/Pagecolumn93

[1]Sasaki;Minamoto;Sugiura;Niwa[JournalofOrganicChemistry,1976,vol.41,#19,p.3138-3143]

[2]Sheng,Jia;Hassan,AbdallaE.A.;Huang,Zhen[JournalofOrganicChemistry,2008,vol.73,#10,p.3725-3729]

[3]CurrentPatentAssignee:CHENGDUPORTONPHARMACEUTICAL;PORTONFINECHEMICALSLIMITED-CN106366145,2017,ALocationinpatent:Paragraph0019

[1]Wakamatsu,Hideaki;Itoh,Moeko;Natori,Yoshihiro;Yoshimura,Yuichi[Nucleosides,nucleotidesandnucleicacids,2020,vol.39,#1-3,p.365-383]

[2]Haraguchi,Kazuhiro;Tanaka,Hiromichi;Maeda,Hideaki;Itoh,Yoshiharu;Saito,Shigeru;Miyasaka,Tadashi[JournalofOrganicChemistry,1991,vol.56,#18,p.5401-5408]

[3]Dunkel;Cook;Acevedo[JournalofHeterocyclicChemistry,1993,vol.30,#5,p.1421-1430]

[4]Robins,M.J.;Trip,E.M.[TetrahedronLetters,1974,p.3369-3372]

[5]Fallois,LoicLeHirde;Decout,Jean-Luc;Fontecave,Marc[TetrahedronLetters,1995,vol.36,#52,p.9479-9480]

[1]Sukeda;Shuto;Sugimoto;Ichikawa;Matsuda[JournalofOrganicChemistry,2000,vol.65,#26,p.8988-8996]

[2]Ogilvie,K.K.;Iwacha,D.[CanadianJournalofChemistry,1974,vol.52,p.1787-1797]

[3]Ogilvie,KelvinK.;McGee,DannyP.C.;Boisvert,SuzanneM.;Hakimelahi,GholamH.;Proba,ZbigniewA.[CanadianJournalofChemistry,1983,vol.61,p.1204-1212]

[1]Cai,Aijie;Liu,Wei;Wang,Chao;Yan,Wenhao[AngewandteChemie-InternationalEdition,2021,vol.60,#52,p.27070-27077][Angew.Chem.,2021,vol.133,#52,p.27276-27283]

[2]Verheyden;Moffatt[JournalofOrganicChemistry,1970,vol.35,#7,p.2319-2326]

Literature

Title: An efficient synthetic approach to 6,5'-(S)- and 6,5'-(R)-cyclouridine.

Journal: Chemical communications (Cambridge, England) 20120607

Title: Influence of conformationally restricted pyrimidines on the activity of 10-23 DNAzymes.

Journal: Bioorganic & medicinal chemistry 20120415

Title: Synthesis and hybridization properties of 2'-O-methylated oligoribonucleotides incorporating 2'-O-naphthyluridines.

Journal: Organic & biomolecular chemistry 20110107

Title: The X-ray structure of Salmonella typhimurium uridine nucleoside phosphorylase complexed with 2,2'-anhydrouridine, phosphate and potassium ions at 1.86 A resolution.

Journal: Acta crystallographica. Section D, Biological crystallography 20100101

Title: Microwave-assisted synthesis of 2'-O-aryluridine derivatives.

Journal: Organic letters 20091217

Title: Synthesis and properties of new RNA molecules incorporating 2'-O-aryluridine derivatives.

Journal: Nucleic acids symposium series (2004) 20090101

Title: Isolation, crystallization and preliminary crystallographic analysis of Salmonella typhimurium uridine phosphorylase crystallized with 2,2'-anhydrouridine.

Journal: Acta crystallographica. Section F, Structural biology and crystallization communications 20071001

Title: Synthesis and anti-viral activity of a series of d- and l-2'-deoxy-2'-fluororibonucleosides in the subgenomic HCV replicon system.

Journal: Bioorganic & medicinal chemistry 20050301

Title: Efficient synthesis of 2',3'-dideoxy-2'-amino-3'-thiouridine.

Journal: Organic letters 20040624

Title: Antiviral and antineoplastic activities of pyrimidine arabinosyl nucleosides and their 5'-amino derivatives.

Journal: Journal of medicinal chemistry 19791001

Title: Drabikowska AK, et al. Inhibitor properties of some 5-substituted uracil acyclonucleosides, and 2,2'-anhydrouridines versus uridine phosphorylase from E. coli and mammalian sources. Biochem Pharmacol. 1987 Dec 1;36(23):4125-8.

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Tags:3736-77-4 Molecular Formula|3736-77-4 MDL|3736-77-4 SMILES|3736-77-4 2,2'-Anhydro-1(B-D-arabinofuranosyl)uracil |Heterocyclic_Building_Blocks |Organic_Building_Blocks