Product Name

  • Name

    6-THIOGUANOSINE

  • EINECS 201-597-2
  • CAS No. 85-31-4
  • Article Data10
  • CAS DataBase
  • Density 2.18 g/cm3
  • Solubility Soluble in Ammonium Hydroxide and water
  • Melting Point 230-231°C
  • Formula C10H13 N5 O4 S
  • Boiling Point 756.9 °C at 760 mmHg
  • Molecular Weight 299.31
  • Flash Point 411.6 °C
  • Transport Information
  • Appearance Yellow-Green Powder
  • Safety Poison by intraperitoneal route. When heated to decomposition it emits very toxic fumes of NOx and SOx. See also MERCAPTANS.
  • Risk Codes
  • Molecular Structure Molecular Structure of 85-31-4 (6-THIOGUANOSINE)
  • Hazard Symbols
  • Synonyms 6H-Purine-6-thione,2-amino-1,9-dihydro-9-b-D-ribofuranosyl- (8CI); 9H-Purine-6(1H)-thione, 2-amino-9-b-D-ribofuranosyl- (6CI,7CI);2-Amino-6-mercaptopurine ribonucleoside; 2-Amino-6-mercaptopurine riboside;2-Amino-9-(b-D-ribofuranosyl)purine-6-thiol;2-Amino-9-b-D-ribofuranosyl-9H-purine-6-thiol;2-Amino-9-b-D-ribofuranosylpurine-6-thione;6-Mercaptoguanine riboside; 6-Mercaptoguanosine; 6-Thioguanine ribonucleoside;6-Thioguanine riboside; 6-Thioguanosine; 9-b-D-Ribofuranosylthioguanine; NSC-29422; Thioguanosine
  • PSA 174.53000
  • LogP -0.73620

Synthetic route

O2',O3',O5'-tribenzoyl-6-thio-guanosine
88010-92-8

O2',O3',O5'-tribenzoyl-6-thio-guanosine

6-thioguanosine
85-31-4

6-thioguanosine

Conditions
ConditionsYield
With sodium ethanolate
G
118-00-3

G

6-thioguanosine
85-31-4

6-thioguanosine

Conditions
ConditionsYield
With pyridine; sodium hydrogensulfide; trifluoroacetic anhydride 1) 40 min, ice-bath, 2) DMF, 24 h; Multistep reaction;
2',3',5'-tri-O-benzoylguanosine
66048-53-1

2',3',5'-tri-O-benzoylguanosine

6-thioguanosine
85-31-4

6-thioguanosine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aqueous pyridine; P2S5
2: ethanolic sodium ethylate
View Scheme
2,4-Dinitrofluorobenzene
70-34-8

2,4-Dinitrofluorobenzene

6-thioguanosine
85-31-4

6-thioguanosine

(2R,3R,4S,5R)-2-[2-Amino-6-(2,4-dinitro-phenylsulfanyl)-purin-9-yl]-5-hydroxymethyl-tetrahydro-furan-3,4-diol
74418-21-6

(2R,3R,4S,5R)-2-[2-Amino-6-(2,4-dinitro-phenylsulfanyl)-purin-9-yl]-5-hydroxymethyl-tetrahydro-furan-3,4-diol

Conditions
ConditionsYield
With triethylamine80%
With triethylamine
6-thioguanosine
85-31-4

6-thioguanosine

6-amino-1-β-D-ribofuranosylimidazo<4,5-c>pyridine-4-sulfenamide
123002-38-0

6-amino-1-β-D-ribofuranosylimidazo<4,5-c>pyridine-4-sulfenamide

Conditions
ConditionsYield
With potassium hydroxide; chloroamine for 0.75h; from 0 deg C to RT;74%
With potassium hydroxide; chloroamine at 0℃; for 1.5h;73.7%
triethylamine carbonate
15715-58-9

triethylamine carbonate

6-thioguanosine
85-31-4

6-thioguanosine

6-thioguanosine 5'-O-monophosphate triethylammonium salt

6-thioguanosine 5'-O-monophosphate triethylammonium salt

Conditions
ConditionsYield
Stage #1: 6-thioguanosine With trimethyl phosphite; trichlorophosphate at 0℃; for 48h;
Stage #2: triethylamine carbonate In water		68%
cobalt(II) nitrate hexahydrate

cobalt(II) nitrate hexahydrate

6-thioguanosine
85-31-4

6-thioguanosine

[Co(6-thioGuo)3] sesquihydrate

[Co(6-thioGuo)3] sesquihydrate

Conditions
ConditionsYield
In methanol; water at 86℃; for 3h;48%
cobalt(II) sulphate heptahydrate

cobalt(II) sulphate heptahydrate

6-thioguanosine
85-31-4

6-thioguanosine

[bis(6-thioguanosine-k2N,S)(6-thioguanosinato-k2N,S)cobalt(III)] sulphate trihydrate

[bis(6-thioguanosine-k2N,S)(6-thioguanosinato-k2N,S)cobalt(III)] sulphate trihydrate

Conditions
ConditionsYield
With sodium hydroxide In water for 3h; pH=8; Reflux;15%
6-thioguanosine
85-31-4

6-thioguanosine

A

thioguanine
154-42-7

thioguanine

B

α-D-ribofuranosyl-1-phosphate
18646-11-2

α-D-ribofuranosyl-1-phosphate

Conditions
ConditionsYield
With E. coli purine nucleoside phosphorylase Enzyme kinetics; Substitution;
6-thioguanosine
85-31-4

6-thioguanosine

N2-phenoxyacetyl-S6-(2,4-dinitrophenyl)-6-thioguanosine
623164-06-7

N2-phenoxyacetyl-S6-(2,4-dinitrophenyl)-6-thioguanosine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 80 percent / triethylamine
2: NH3 / H2O
View Scheme
Multi-step reaction with 4 steps
1: Et3N
2: pyridine
3: pyridine
4: aq. NH3
View Scheme
6-thioguanosine
85-31-4

6-thioguanosine

9-((2R,3R,4R,5R)-3,4-Bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-6-(2,4-dinitro-phenylsulfanyl)-9H-purin-2-ylamine

9-((2R,3R,4R,5R)-3,4-Bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-6-(2,4-dinitro-phenylsulfanyl)-9H-purin-2-ylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 80 percent / triethylamine
View Scheme
Multi-step reaction with 2 steps
1: Et3N
2: pyridine
View Scheme
6-thioguanosine
85-31-4

6-thioguanosine

N-[9-(3,4-bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-6-(2,4-dinitro-phenylsulfanyl)-9H-purin-2-yl]-2-phenoxy-acetamide

N-[9-(3,4-bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-6-(2,4-dinitro-phenylsulfanyl)-9H-purin-2-yl]-2-phenoxy-acetamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 80 percent / triethylamine
View Scheme
Multi-step reaction with 3 steps
1: Et3N
2: pyridine
3: pyridine
View Scheme
6-thioguanosine
85-31-4

6-thioguanosine

N-[9-{3,4-dihydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-6-(2,4-dinitro-phenylsulfanyl)-9H-purin-2-yl]-2-phenoxy-acetamide
623164-07-8

N-[9-{3,4-dihydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-6-(2,4-dinitro-phenylsulfanyl)-9H-purin-2-yl]-2-phenoxy-acetamide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 80 percent / triethylamine
2: NH3 / H2O
3: pyridine
View Scheme
Multi-step reaction with 5 steps
1: Et3N
2: pyridine
3: pyridine
4: aq. NH3
5: pyridine
View Scheme
6-thioguanosine
85-31-4

6-thioguanosine

N-[9-{3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-6-(2,4-dinitro-phenylsulfanyl)-9H-purin-2-yl]-2-phenoxy-acetamide
623164-08-9

N-[9-{3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-6-(2,4-dinitro-phenylsulfanyl)-9H-purin-2-yl]-2-phenoxy-acetamide

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 80 percent / triethylamine
2: NH3 / H2O
3: pyridine
4: pyridine; AgNO3
View Scheme
Multi-step reaction with 6 steps
1: Et3N
2: pyridine
3: pyridine
4: aq. NH3
5: pyridine
6: AgNO3; pyridine
View Scheme
6-thioguanosine
85-31-4

6-thioguanosine

Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-[6-(2,4-dinitro-phenylsulfanyl)-2-(2-phenoxy-acetylamino)-purin-9-yl]-2-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester

Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-[6-(2,4-dinitro-phenylsulfanyl)-2-(2-phenoxy-acetylamino)-purin-9-yl]-2-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 80 percent / triethylamine
2: NH3 / H2O
3: pyridine
4: pyridine; AgNO3
5: N,N-di(isopropyl)ethylamine
View Scheme
Multi-step reaction with 7 steps
1: Et3N
2: pyridine
3: pyridine
4: aq. NH3
5: pyridine
6: AgNO3; pyridine
7: i-Pr2NEt / 12 h / 10 °C
View Scheme
6-thioguanosine
85-31-4

6-thioguanosine

N-[9-{4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-6-(2,4-dinitro-phenylsulfanyl)-9H-purin-2-yl]-2-phenoxy-acetamide

N-[9-{4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-6-(2,4-dinitro-phenylsulfanyl)-9H-purin-2-yl]-2-phenoxy-acetamide

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: Et3N
2: pyridine
3: pyridine
4: aq. NH3
5: pyridine
6: AgNO3; pyridine
View Scheme
6-thioguanosine
85-31-4

6-thioguanosine

N-[9-{3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-6-(2,4-dinitro-phenylsulfanyl)-9H-purin-2-yl]-2-phenoxy-acetamide

N-[9-{3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-6-(2,4-dinitro-phenylsulfanyl)-9H-purin-2-yl]-2-phenoxy-acetamide

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: Et3N
2: pyridine
3: pyridine
4: aq. NH3
5: pyridine
6: AgNO3; pyridine
View Scheme
6-thioguanosine
85-31-4

6-thioguanosine

2-amino-9-β-D-ribofuranosylpurine-6-sulfonamide
123002-39-1

2-amino-9-β-D-ribofuranosylpurine-6-sulfonamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 74 percent / chloramine, 2 N KOH / 0.75 h / from 0 deg C to RT
2: 86.7 percent / m-chloroperoxybenzoic acid (MCPBA) / aq. ethanol / 18 h / Ambient temperature
View Scheme
6-thioguanosine
85-31-4

6-thioguanosine

(RS)-2-amino-9-β-D-ribofuranosylpurine-6-sulfinamide
124508-99-2

(RS)-2-amino-9-β-D-ribofuranosylpurine-6-sulfinamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 73.7 percent / ClNH2, 2 N KOH / 1.5 h / 0 °C
2: 67 percent / 85percent 3-chloroperoxybenzoic acid / ethanol / 0.25 h / 0 - 5 °C
View Scheme
6-thioguanosine
85-31-4

6-thioguanosine

(R)-2-amino-9-β-D-ribofuranosylpurine-6-sulfinamide
123002-46-0

(R)-2-amino-9-β-D-ribofuranosylpurine-6-sulfinamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 74 percent / chloramine, 2 N KOH / 0.75 h / from 0 deg C to RT
2: 1.) m-chloroperoxybenzoic acid (MCPBA) / ethanol; H2O / 19 h / Ambient temperature
View Scheme
6-thioguanosine
85-31-4

6-thioguanosine

(S)-2-amino-9-β-D-ribofuranosylpurine-6-sulfinamide
123002-47-1

(S)-2-amino-9-β-D-ribofuranosylpurine-6-sulfinamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 74 percent / chloramine, 2 N KOH / 0.75 h / from 0 deg C to RT
2: 1.) m-chloroperoxybenzoic acid (MCPBA) / ethanol; H2O / 19 h / Ambient temperature
View Scheme
6-thioguanosine
85-31-4

6-thioguanosine

C10H12Cl2N5O5PS

C10H12Cl2N5O5PS

Conditions
ConditionsYield
Stage #1: 6-thioguanosine With trimethyl phosphite; lutidine at 0℃; for 0.166667h;
Stage #2: With trichlorophosphate for 1h;
With trimethyl phosphite; trichlorophosphate
bis(cyclopentadienyl)titanium dichloride
1271-19-8

bis(cyclopentadienyl)titanium dichloride

6-thioguanosine
85-31-4

6-thioguanosine

Ti(C5H5)2(6-thioguanineribose) dichloride complex

Ti(C5H5)2(6-thioguanineribose) dichloride complex

Conditions
ConditionsYield
In methanol under N2 either in glove box or in double-manifold vac.; 1 equiv. of 6-thioguanineribose; mixted at room temp.; mixt. stirred for 8-12 h; solid isolated in fritted funnel of fine porosity; dried in vac. at 45°C for 12 h; elem. anal.;
bis(cyclopentadienyl)molybdenum(IV) dichloride
12184-22-4

bis(cyclopentadienyl)molybdenum(IV) dichloride

6-thioguanosine
85-31-4

6-thioguanosine

[(η5-cyclopentadienyl)2Mo((-)-2-amino-6-mercaptopurine riboside)]Cl2

[(η5-cyclopentadienyl)2Mo((-)-2-amino-6-mercaptopurine riboside)]Cl2

Conditions
ConditionsYield
In tetrahydrofuran; methanol stirring at room temp. for 8 h; ppt. was filtered off, washed with cold THF, dried in vac., recrystd. from cold MeOH, dried in vac. for 12 h at 30°C; elem. anal.;
6-thioguanosine
85-31-4

6-thioguanosine

C22H32N10O17P3S(1+)*3C6H15N

C22H32N10O17P3S(1+)*3C6H15N

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: trimethyl phosphite; trichlorophosphate / 48 h / 0 °C
2: 2,2'-dipyridyldisulphide; triethylamine; triphenylphosphine / N,N-dimethyl-formamide
3: zinc(II) chloride / N,N-dimethyl-formamide
View Scheme
6-thioguanosine
85-31-4

6-thioguanosine

6-thioguanosine 5'-O-phosphorimidazolide lithium salt
1616389-41-3

6-thioguanosine 5'-O-phosphorimidazolide lithium salt

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: trimethyl phosphite; trichlorophosphate / 48 h / 0 °C
2: 2,2'-dipyridyldisulphide; triethylamine; triphenylphosphine / N,N-dimethyl-formamide
View Scheme
6-thioguanosine
85-31-4

6-thioguanosine

C22H32N10O16P3S2(1+)*3C6H15N

C22H32N10O16P3S2(1+)*3C6H15N

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: trimethyl phosphite; trichlorophosphate / 48 h / 0 °C
2: 2,2'-dipyridyldisulphide; triethylamine; triphenylphosphine / N,N-dimethyl-formamide
3: zinc(II) chloride / N,N-dimethyl-formamide
View Scheme
6-thioguanosine
85-31-4

6-thioguanosine

C22H29N10O17P3S(2-)*3Na(1+)

C22H29N10O17P3S(2-)*3Na(1+)

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: trimethyl phosphite; trichlorophosphate / 48 h / 0 °C
2: 2,2'-dipyridyldisulphide; triethylamine; triphenylphosphine / N,N-dimethyl-formamide
3: zinc(II) chloride / N,N-dimethyl-formamide
4: sodium perchlorate / water; acetone
View Scheme

6-Thioguanosine Chemical Properties

Molecular Formula: C10H13N5O4S
Molar mass: 299.31 g/mol
EINECS: 201-597-2
Density: 2.18 g/cm3
Flash Point: 411.6 °C
Index of Refraction: 1.975
Boiling Point: 756.9 °C at 760 mmHg
Vapour Pressure: 4.44E-24 mmHg at 25°C
Melting point: 230-231°C
Appearance: Tan powder
Product categories of 6-Thioguanosine (85-31-4): Nucleotides and Nucleosides;Sulfur & Selenium Compounds;Bases & Related Reagents;Nucleotides
Structure of 6-Thioguanosine (85-31-4):

XLogP3-AA: -1.2
H-Bond Donor: 5
H-Bond Acceptor: 7
Systematic Name: 2-Amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-3H-purine-6-thione 
SMILES: S=C3/N=C(/N)Nc1c3ncn1[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)CO 
InChI: InChI=1/C10H13N5O4S/c11-10-13-7-4(8(20)14-10)12-2-15(7)9-6(18)5(17)3(1-16)19-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,20)/t3-,5-,6-,9-/m1/s1 
InChIKey: OTDJAMXESTUWLO-UUOKFMHZBV 
Std. InChI: InChI=1S/C10H13N5O4S/c11-10-13-7-4(8(20)14-10)12-2-15(7)9-6(18)5(17)3(1-16)19-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,20)/t3-,5-,6-,9-/m1/s1 
Std. InChIKey: OTDJAMXESTUWLO-UUOKFMHZSA-N

6-Thioguanosine Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD10 unreported 1700mg/kg (1700mg/kg)   Progress in Medical Chemistry. Vol. 7, Pg. 69, 1970.
mouse LD50 intraperitoneal 156mg/kg (156mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
rat LD50 intraperitoneal 200mg/kg (200mg/kg)   Advances in Teratology. Vol. 3, Pg. 181, 1968.

6-Thioguanosine Safety Profile

Poison by intraperitoneal route. When heated to decomposition it emits very toxic fumes of NOx and SOx. See also MERCAPTANS.

6-Thioguanosine Specification

 6-Thioguanosine (85-31-4) also can be called 2-Amino-6-mercapto-9-b-D-ribofuranosylpurinee ; 6H-Purine-6-thione, 2-amino-1,9-dihydro-9-.beta.-D-ribofuranosyl- ; 2-Amino-9-(.beta.-D-ribofuranosyl)purine-6-thiol ; 9H-Purine-6-thiol, 2-amino-9-.beta.-D-ribofuranosyl- ; 2-Amino-6-mercapto-9-(.beta.-D-ribofuranosyl)purine ; and ; 6-Mercaptoguanosine .

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