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  2. 85326-06-3
Dideoxyguanosine | 85326-06-3

Product name:Dideoxyguanosine

CAS No:85326-06-3
MF:C10H13N5O3
MW:251.241921186447
MDL:MFCD00057074
CID:60865
Names and Identifiers
  • 2-Amino-9-((2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-purin-6(9H)-one
  • 2-Amino-9-[5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one
  • 2',3'-Dideoxyguanosine
  • 2-amino-9-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one
  • Guanosine, 2',3'-dideoxy-
  • Dideoxyguanosine
  • ddGuo
  • 2',3'-Didioxyguanosine
  • NSC619072
  • 2-amino-9-[(2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1H-purin-6-one
  • deoxy-deoxy-guanosine
  • 2', 3'-Dideoxyguanosine
  • 2'',3''-Dideoxyguanosine
  • 3234AC
  • AX8012129
  • 2′,3′-Dideoxyguanosine (ACI)
  • MDL:MFCD00057074
  • InChIKey:OCLZPNCLRLDXJC-NTSWFWBYSA-N
  • Inchi:1S/C10H13N5O3/c11-10-13-8-7(9(17)14-10)12-4-15(8)6-2-1-5(3-16)18-6/h4-6,16H,1-3H2,(H3,11,13,14,17)/t5-,6+/m0/s1
  • SMILES:O=C1N=C(N)NC2N([C@H]3CC[C@@H](CO)O3)C=NC1=2
Chemical and Physical Properties

Computed Properties

  • Exact Mass: 251.10200
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 5
  • Rotatable Bond Count: 2
  • Heavy Atom Count: 18
  • Complexity: 388
  • Isotope Atom Count: 0
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Covalently-Bonded Unit Count: 1
  • XLogP3: -0.9
  • Tautomer Count: 9
  • Surface Charge: 0
  • Topological Polar Surface Area: 115

Experimental Properties

  • LogP: -0.04710
  • PSA: 119.05000
  • Boiling Point: 632.1°C at 760 mmHg
Security Information
  • WGK Germany:3
  • Safety Instruction:24/25
Synthetic Circuit

Synthetic Circuit 1

Reaction Conditions
1.1 -
2.1 Solvents: Acetonitrile ;  10 min, -45 °C; 1 h, cooled; 20 h, rt
3.1 Reagents: Zinc Solvents: Dimethylformamide ;  1 h, rt
4.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ;  12 h, 0.4 MPa, rt
5.1 Reagents: Methylamine Solvents: Methanol ;  5 h, rt
Reference
Synthesis and Anti-HIV Activity of a Series of 6-Modified 2',3'-dideoxyguanosine and 2',3'-didehydro-2',3'-dideoxyguanosine Analogs
Xie, Lujia; et al, Chinese Journal of Chemistry, 2013, 31(9), 1207-1218

Synthetic Circuit 2

Reaction Conditions
1.1 Reagents: 2-(Acetyloxy)-2-methylpropanoyl bromide Solvents: Acetonitrile ,  Water ;  1 h, rt
1.2 Reagents: Zinc alloy, base, Zn,Cu ;  10 min, rt
2.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ;  rt
Reference
Crystal structure of metacavir ethanol solvent compound
Liu, Cai-lian; et al, Huaxue Shiji, 2013, 35(1), 52-54

Synthetic Circuit 3

Reaction Conditions
1.1 Reagents: Hexamethyldisilazane Solvents: Dimethylformamide
1.2 Solvents: Pyridine
1.3 Reagents: Methanol
2.1 Reagents: Imidazole Solvents: Dimethylformamide
3.1 Solvents: Dimethylformamide
4.1 Reagents: 1,3-Dimethyl-2-phenyl-1,3,2-diazaphospholidine
5.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran
6.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol
7.1 Reagents: Ammonia Solvents: Methanol
Reference
General syntheses of 2',3'-dideoxynucleosides and 2',3'-didehydro-2',3'-dideoxynucleosides
Chu, C. K.; et al, Journal of Organic Chemistry, 1989, 54(9), 2217-25

Synthetic Circuit 4

Reaction Conditions
1.1 Reagents: Pyridine ,  Tetrabutylammonium fluoride Solvents: Tetrahydrofuran
Reference
Synthesis and 1H and 13C NMR spectral characteristics of 8-bromo-2',3'-dideoxyguanosine and 8-bromo-2',3'-dideoxyinosine
Zeidler, Joanna; et al, Nucleosides & Nucleotides, 1996, 15(5), 1077-1095

Synthetic Circuit 5

Reaction Conditions
1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ;  12 h, 0.4 MPa, rt
2.1 Reagents: Methylamine Solvents: Methanol ;  5 h, rt
Reference
Synthesis and Anti-HIV Activity of a Series of 6-Modified 2',3'-dideoxyguanosine and 2',3'-didehydro-2',3'-dideoxyguanosine Analogs
Xie, Lujia; et al, Chinese Journal of Chemistry, 2013, 31(9), 1207-1218

Synthetic Circuit 6

Reaction Conditions
1.1 -
2.1 Catalysts: Adenosine deaminase Solvents: Water
Reference
Enzymic synthesis of 2',3'-dideoxyguanosine
Nair, Vasu; et al, Synlett, 1991, (10), 753-4

Synthetic Circuit 7

Reaction Conditions
1.1 Reagents: Azobisisobutyronitrile ,  Tributylstannane Solvents: 1,4-Dioxane
2.1 Reagents: Pyridine ,  Tetrabutylammonium fluoride Solvents: Tetrahydrofuran
Reference
Synthesis and 1H and 13C NMR spectral characteristics of 8-bromo-2',3'-dideoxyguanosine and 8-bromo-2',3'-dideoxyinosine
Zeidler, Joanna; et al, Nucleosides & Nucleotides, 1996, 15(5), 1077-1095

Synthetic Circuit 8

Reaction Conditions
1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ;  rt
Reference
Crystal structure of metacavir ethanol solvent compound
Liu, Cai-lian; et al, Huaxue Shiji, 2013, 35(1), 52-54

Synthetic Circuit 9

Reaction Conditions
1.1 -
2.1 -
3.1 Catalysts: Adenosine deaminase Solvents: Water
Reference
Enzymic synthesis of 2',3'-dideoxyguanosine
Nair, Vasu; et al, Synlett, 1991, (10), 753-4

Synthetic Circuit 10

Reaction Conditions
1.1 Catalysts: Adenosine deaminase ;  48 h
Reference
Coupled biocatalysts applied to the synthesis of nucleosides
Medici, Rosario; et al, Nucleic Acids Symposium Series, 2008, 52(1), 541-542

Synthetic Circuit 11

Reaction Conditions
1.1 Solvents: Dimethylformamide
1.2 -
2.1 -
Reference
A novel and efficient preparation of 2',3'-dideoxynucleosides
Prisbe, Ernest J.; et al, Synthetic Communications, 1985, 15(5), 401-9

Synthetic Circuit 12

Reaction Conditions
1.1 Reagents: Ammonia Solvents: Methanol
Reference
General syntheses of 2',3'-dideoxynucleosides and 2',3'-didehydro-2',3'-dideoxynucleosides
Chu, C. K.; et al, Journal of Organic Chemistry, 1989, 54(9), 2217-25

Synthetic Circuit 13

Reaction Conditions
1.1 Reagents: Azobisisobutyronitrile ,  Dibutyltin oxide Solvents: 1,4-Dioxane
1.2 Reagents: Ammonium hydroxide Solvents: Methanol
Reference
A novel and efficient preparation of 2',3'-dideoxynucleosides
Prisbe, Ernest J.; et al, Synthetic Communications, 1985, 15(5), 401-9

Synthetic Circuit 14

Reaction Conditions
Reference
A novel and efficient preparation of 2',3'-dideoxynucleosides
Prisbe, Ernest J.; et al, Synthetic Communications, 1985, 15(5), 401-9

Synthetic Circuit 15

Reaction Conditions
1.1 Solvents: Dimethylformamide
1.2 -
2.1 Reagents: Azobisisobutyronitrile ,  Dibutyltin oxide Solvents: 1,4-Dioxane
2.2 Reagents: Ammonium hydroxide Solvents: Methanol
Reference
A novel and efficient preparation of 2',3'-dideoxynucleosides
Prisbe, Ernest J.; et al, Synthetic Communications, 1985, 15(5), 401-9

Synthetic Circuit 16

Reaction Conditions
1.1 Catalysts: Adenosine deaminase Solvents: Water
Reference
Enzymic synthesis of 2',3'-dideoxyguanosine
Nair, Vasu; et al, Synlett, 1991, (10), 753-4

Synthetic Circuit 17

Reaction Conditions
1.1 Reagents: Methylamine Solvents: Methanol ;  5 h, rt
Reference
Synthesis and Anti-HIV Activity of a Series of 6-Modified 2',3'-dideoxyguanosine and 2',3'-didehydro-2',3'-dideoxyguanosine Analogs
Xie, Lujia; et al, Chinese Journal of Chemistry, 2013, 31(9), 1207-1218

Synthetic Circuit 18

Reaction Conditions
1.1 Catalysts: Adenosine deaminase Solvents: Water ;  48 h, pH 7, 37 °C
Reference
Arthrobacter oxydans as a biocatalyst for purine deamination
Medici, Rosario; et al, FEMS Microbiology Letters, 2008, 289(1), 20-26
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