Product Name

  • Name

    6-THIO-2'-DEOXYGUANOSINE

  • EINECS
  • CAS No. 789-61-7
  • Article Data8
  • CAS DataBase
  • Density 2.02g/cm3
  • Solubility
  • Melting Point 190-192 °C
  • Formula C10H13 N5 O3 S
  • Boiling Point 709.1°C at 760 mmHg
  • Molecular Weight 283.311
  • Flash Point 382.6°C
  • Transport Information
  • Appearance
  • Safety Questionable carcinogen with experimental carcinogenic data reported. When heated to decomposition it emits toxic vapors of NOx and SOx.
  • Risk Codes
  • Molecular Structure Molecular Structure of 789-61-7 (6-THIO-2'-DEOXYGUANOSINE)
  • Hazard Symbols Questionable carcinogen.
  • Synonyms 9H-Purine-6(1H)-thione,2-amino-9-(2-deoxy-b-D-erythro-pentofuranosyl)- (7CI,8CI);2'-Deoxy-6-thioguanosine;2'-Deoxythioguanosine;2'-Desoxy-6-thioguanosine;NSC71261;TGdR;Thioguanine deoxyriboside;b-Thioguanine deoxyriboside;
  • PSA 154.30000
  • LogP 0.29300

Synthetic route

Isobutyric acid (2R,3S,5R)-5-(2-isobutyrylamino-6-thioxo-1,6-dihydro-purin-9-yl)-2-isobutyryloxymethyl-tetrahydro-furan-3-yl ester
136112-93-1

Isobutyric acid (2R,3S,5R)-5-(2-isobutyrylamino-6-thioxo-1,6-dihydro-purin-9-yl)-2-isobutyryloxymethyl-tetrahydro-furan-3-yl ester

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine
789-61-7

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine

Conditions
ConditionsYield
With sodium hydroxide In ethanol100%
2'-Deoxyguanosine
961-07-9

2'-Deoxyguanosine

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine
789-61-7

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine

Conditions
ConditionsYield
With sodium hydrogensulfide; trifluoroacetic anhydride In pyridine; N,N-dimethyl-formamide65%
With pyridine; sodium hydrogensulfide; trifluoroacetic anhydride 1) 40 min, ice-bath, 2) DMF, 24 h; Yield given. Multistep reaction;
2-Amino-6-chloro-9-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)purine
35095-93-3

2-Amino-6-chloro-9-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)purine

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine
789-61-7

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine

Conditions
ConditionsYield
With hydrogen sulfide; sodium methylate 1) anhydr. MeOH, reflux, 2 h; 2) MeOH, reflux, 1 h; Yield given. Multistep reaction;
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
4330-21-6

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine
789-61-7

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 51 percent / 1) sodium hydride (60percent in oil) / 1) acetonitrile, RT, 30 min; 2) acetonitrile, 20 h
2: 1) H2S/1M sodium methoxide; 2) 1M sodium methoxide / 1) anhydr. MeOH, reflux, 2 h; 2) MeOH, reflux, 1 h
View Scheme
2-Amino-6-chloropurin
10310-21-1

2-Amino-6-chloropurin

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine
789-61-7

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 51 percent / 1) sodium hydride (60percent in oil) / 1) acetonitrile, RT, 30 min; 2) acetonitrile, 20 h
2: 1) H2S/1M sodium methoxide; 2) 1M sodium methoxide / 1) anhydr. MeOH, reflux, 2 h; 2) MeOH, reflux, 1 h
View Scheme
2'-deoxy-N2-isobutyrylguanosine 3',5'-diisobutyrate
82921-42-4

2'-deoxy-N2-isobutyrylguanosine 3',5'-diisobutyrate

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine
789-61-7

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1. triethylamine, dimethylaminopyridine, mesitylenesulphonyl chloride, 2a. N-methyl pyrrolidine, 2b. thiolacetic acid / 1. CH2Cl2, RT, 2a. ice bath, 2b. 30 min
2: 100 percent / 2 M NaOH / ethanol
View Scheme
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine
789-61-7

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine-6-sulfenamide
124416-63-3

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine-6-sulfenamide

Conditions
ConditionsYield
With potassium hydroxide; sodium hydroxide; sodium hypochlorite In water 0 deg C to RT;86%
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine
789-61-7

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine

2-amino-9-(β-D-2'-deoxyribofuranosyl)-purine
3616-24-8

2-amino-9-(β-D-2'-deoxyribofuranosyl)-purine

Conditions
ConditionsYield
nickel In ethanol; water desulfuration; Heating;77%
With nickel75%
With nickel In water at 50℃; for 13h;73%
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine
789-61-7

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine

triethylamine
121-44-8

triethylamine

2'-deoxy-6-thioguanosine-5'-triphosphate triethylammonium salt

2'-deoxy-6-thioguanosine-5'-triphosphate triethylammonium salt

Conditions
ConditionsYield
Stage #1: 2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine With phosphorous acid trimethyl ester; trichlorophosphate at 0℃; for 3h; phosphorylation;
Stage #2: triethylamine With tributyl-amine; bis(tri-n-butylammonium) pyrophosphate In N,N-dimethyl-formamide pH=7.0; phosphorylation;		38%
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine
789-61-7

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine

cobalt(II) nitrate hexahydrate

cobalt(II) nitrate hexahydrate

[Co(2'-deoxy-6-thioguanine)3](NO3)2 dihydrate

[Co(2'-deoxy-6-thioguanine)3](NO3)2 dihydrate

Conditions
ConditionsYield
In methanol at 60℃; for 24h;31%
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine
789-61-7

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine

methyl iodide
74-88-4

methyl iodide

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-(methylthio)purine
37113-42-1

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-(methylthio)purine

Conditions
ConditionsYield
In ammonium hydroxide other conditions: phosphate aq. solution, pH 8.5;
With ammonium hydroxide for 0.666667h; Ambient temperature;90 mg
With ammonium hydroxide for 1.5h;
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine
789-61-7

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine

A

thioguanine
154-42-7

thioguanine

B

2-deoxy–α-D-ribose 1-phosphate
17039-17-7

2-deoxy–α-D-ribose 1-phosphate

Conditions
ConditionsYield
With E. coli purine nucleoside phosphorylase Enzyme kinetics; Substitution;
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine
789-61-7

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine

9-(2-deoxy-β-D-ribofuranosyl)purine-2-thione

9-(2-deoxy-β-D-ribofuranosyl)purine-2-thione

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 77 percent / Raney nickel / H2O; ethanol / Heating
2: 80 percent / pyridine / 2 h
3: 35 percent / SbCl3; tert-butyl nitrite / CH2Cl2 / 4 h / -5 °C
4: pyridine / 72 h / 75 °C
5: 40 percent / NH3; 2-mercaptoethanol / methanol / 24 h / 20 °C
View Scheme
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine
789-61-7

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine

2-chloro-9-(2-deoxy-3,5-diisobutyryl-β-D-ribofuranosyl)purine
273721-25-8

2-chloro-9-(2-deoxy-3,5-diisobutyryl-β-D-ribofuranosyl)purine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 77 percent / Raney nickel / H2O; ethanol / Heating
2: 80 percent / pyridine / 2 h
3: 35 percent / SbCl3; tert-butyl nitrite / CH2Cl2 / 4 h / -5 °C
View Scheme
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine
789-61-7

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine

(R,S)-2-amino-9-(2-deoxy-β-D-erythro-pentafuranosyl)purine-6-sulfinamide
124416-58-6

(R,S)-2-amino-9-(2-deoxy-β-D-erythro-pentafuranosyl)purine-6-sulfinamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 86 percent / NaOCl, NaOH, 2N KOH / H2O / 0 deg C to RT
2: 69 percent / MCPBA / CH2Cl2; ethanol / 1.5 h / 0 deg C to RT
View Scheme
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine
789-61-7

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine-6-sulfonamide
124416-64-4

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine-6-sulfonamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 86 percent / NaOCl, NaOH, 2N KOH / H2O / 0 deg C to RT
2: 50 percent / MCPBA / ethanol / Ambient temperature
View Scheme
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine
789-61-7

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine

chloroamine
12190-75-9

chloroamine

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine-6-sulfenamide
124416-63-3

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine-6-sulfenamide

Conditions
ConditionsYield
With sodium hypochlorite In potassium hydroxide; ammonium hydroxide; ethanol2.5 g (84%)
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine
789-61-7

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine

trifluoroethylamine
753-90-2

trifluoroethylamine

2-amino-N6-(2,2,2-trifluoroethyl)-2'-deoxyadenosine

2-amino-N6-(2,2,2-trifluoroethyl)-2'-deoxyadenosine

Conditions
ConditionsYield
With sodium periodate at 50℃; for 1h; Darkness;

Thioguanine deoxyriboside Chemical Properties

IUPAC Name: 2-Amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purine-6-thione
Molecular Formula: C10H13N5O3S
Molecular Weight: 283.34g/mol
Freely Rotating Bonds: 4
Polar Surface Area: 96.44 Å2
Index of Refraction: 1.93
Molar Refractivity: 66.43 cm3
Molar Volume: 139.5 cm3
Polarizability: 26.33 ×10-24cm3
Surface Tension: 95.1 dyne/cm
Density: 2.02 g/cm3
Flash Point: 382.6 °C
Enthalpy of Vaporization: 108.88 kJ/mol
Boiling Point: 709.1 °C at 760 mmHg
Vapour Pressure: 4.22E-21 mmHg at 25°C
The Cas Register Number of Thioguanine deoxyriboside is 789-61-7 .The chemical synonyms of Thioguanine deoxyriboside (CAS No.789-61-7) are 2’-Deoxy-6-thio-guanosin ; 2’-Deoxythioguanosine ; 2-Amino-9-(2-deoxy-beta-d-erythro-pentofuranosyl)-9h-purine-6(1h)-thion ; Beta-2’-deoxythioguanosine ; Beta-thioguaninedeoxyriboside ; Nci-c01581 ; Tgdr ; 6-Thio-2'-deoxyguanosine .The molecular structure of Thioguanine deoxyriboside (CAS No.789-61-7) is.

Thioguanine deoxyriboside Consensus Reports

NCI Carcinogenesis Bioassay (ipr). clear evidence: rat, NCITR*    National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-TR-57 ,1978. ; NCI Carcinogenesis Bioassay (ipr). inadequate studies:mouse, NCITR*    National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-TR-57 ,1978.

Thioguanine deoxyriboside Safety Profile

Questionable carcinogen with experimental carcinogenic data reported. When heated to decomposition it emits toxic vapors of NOx and SOx.

Thioguanine deoxyriboside Specification

The extinguishing agent of Thioguanine deoxyriboside (CAS No.789-61-7) are dry powder, foam, sand, carbon dioxide, water mist.

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