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73-03-0

Basic Information
CAS No.: 73-03-0
Name: Cordycepin
Article Data: 55
Cas Database
Molecular Structure:
Molecular Structure of 73-03-0 (Cordycepin)
Formula: C10H13N5O3
Molecular Weight: 251.245
Synonyms: Cordycepin(6CI,7CI);3'-Deoxyadenosine;9-(3-Deoxy-b-D-ribofuranosyl)adenine;9-Cordyceposidoadenine;9H-Purin-6-amine, 9-(3-deoxy-b-D-erythro-pentofuranosyl)-;Cordycepine;b-D-erythro-Pentofuranoside,adenine-9 3-deoxy-;
EINECS: 200-791-4
Density: 1.91 g/cm3
Melting Point: 225-229 °C
Boiling Point: 627.2 °C at 760 mmHg
Flash Point: 333.1 °C
Solubility: N/A
Appearance: crystalline solid
Hazard Symbols: HarmfulXn,ToxicT
Risk Codes: 40-36/37/38-25-20/21/22
Safety: 22-36-45-26
Transport Information: UN 2811
PSA: 119.31000
LogP: -0.36960
Synthetic route

5'-O-(o-toluoyl)-2'-O-acetyl-3'-deoxy-6-chloropurine

73-03-0

cordycepin

Conditions
ConditionsYield
With ammonia In methanol; ethanol at -20℃; for 48h;100%
2627-64-7

9-(2,3-anhydro-β-D-ribofuranosyl)adenine

73-03-0

cordycepin

Conditions
ConditionsYield
With lithium triethylborohydride In tetrahydrofuran; dimethyl sulfoxide 1.) 4 deg C, 1 h, 2.) 19-22 deg C, overnight;98%
With lithium triethylborohydride In dimethyl sulfoxide53%
With lithium triethylborohydride; acetic acid 1.) Me2SO, THF, 1 h ice-water cooling, then -> room temperature, 2.) H2O; Yield given. Multistep reaction;
116285-72-4

9-((2R,3R,5S)-3-((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydrofuran-2-yl)-9H-purin-6-amine

73-03-0

cordycepin

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃;98%

C14H16ClN5O5

73-03-0

cordycepin

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen In methanol at 25℃; under 37503.8 Torr; for 8h;95%
4395-38-4

N6,2',5'-tribenzoyl-3'-deoxyadenosine

73-03-0

cordycepin

Conditions
ConditionsYield
With sodium methylate In methanol for 1h; Heating;94%
71196-28-6

((2S,4R,5R)-4-acetoxy-5-(6-amino-9H-purin-9-yl)tetrahydrofuran-2-yl)methyl acetate

73-03-0

cordycepin

Conditions
ConditionsYield
With ammonia In methanol for 3h; Ambient temperature;93%
With potassium carbonate In methanol; water at 20℃; for 3h;93%
With methanol; ammonia at 0 - 60℃; for 16h;90%
Stage #1: ((2S,4R,5R)-4-acetoxy-5-(6-amino-9H-purin-9-yl)tetrahydrofuran-2-yl)methyl acetate With sodium hydroxide In methanol at 25℃; for 1h;
Stage #2: With ammonium chloride In methanol for 0.5h; Reagent/catalyst;
87%
101857-01-6

6-N-5'-O-Bis-<4-methoxytriphenylmethyl>-3'-deoxyadenosine

73-03-0

cordycepin

Conditions
ConditionsYield
With acetic acid at 20℃; for 12h;92%
117068-51-6

(2R,3R,5S)-2-(6-amino-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)tetrahydrofuran-3-ol

73-03-0

cordycepin

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 25℃; for 0.5h;91%
90813-62-0

9-(3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)adenine

73-03-0

cordycepin

Conditions
ConditionsYield
With acetic acid In methanol; dichloromethane at 20℃; for 4h; pH=Ca. 4;90%
51763-58-7

9-<5-O-(monomethoxytrityl)-3-deoxy-β-D-erythro-pentofuranosyl>adenine

73-03-0

cordycepin

Conditions
ConditionsYield
With acetic acid at 20℃; for 2h;85%
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Chemistry

Molecular Structure of Cordycepin (CAS NO.73-03-0):

IUPAC Name: (2R,3R,5S)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-ol 
Empirical Formula: C10H13N5O3
Molecular Weight: 251.2419
H bond acceptors: 8
H bond donors: 4
Freely Rotating Bonds: 4
Polar Surface Area: 74.53Å2
Index of Refraction: 1.863
Molar Refractivity: 59.1 cm3
Molar Volume: 130.8 cm3
Surface Tension: 93.6 dyne/cm
Density: 1.91 g/cm3
Flash Point: 333.1 °C
Enthalpy of Vaporization: 97.57 kJ/mol
Boiling Point: 627.2 °C at 760 mmHg
Vapour Pressure: 1.36E-16 mmHg at 25°C
EINECS: 200-791-4
Melting Point: 225-229 °C
Storage temp: -20 °C
Merck: 13,2555
Product Categories: Miscellaneous Natural Products; Bases & Related Reagents; Intermediates & Fine Chemicals; Nucleotides; PharmaceuticalsIn
ChI
InChI=1/C10H13N5O3/c11-8-7-9(13-3-12-8)15(4-14-7)10-6(17)1-5(2-16)18-10/h3-6,10,16-17H,1-2H2,(H2,11,12,13)/t5-,6+,10+/m0/s1
Smiles
n1(c2c(c(ncn2)N)nc1)[C@@H]1O[C@H](CO)C[C@H]1O

Toxicity Data With Reference

1.    

oms-nml:lng 100 µmol/L

    CARYAB    Caryologia. 28 (1975),301.
2.    

dnd-hmn:fbr 500 µmol/L

    ENMUDM    Environmental Mutagenesis. 7 (1985),267.
3.    

dni-hmn:hla 20 mg/L

    JANTAJ    Journal of Antibiotics. 35 (1982),119.

Consensus Reports

EPA Genetic Toxicology Program.

Safety Profile

Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
Safety information of Cordycepin (CAS NO.73-03-0):
Hazard Codes: Xn,T
Risk Statements:
40  Limited evidence of a carcinogenic effect
36/37/38: Irritating to eyes, respiratory system and skin
25  Toxic if swallowed
20/21/22: Harmful by inhalation, in contact with skin and if swallowed
Safety Statements:
22: Do not breathe dust
36: Wear suitable protective clothing
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
RIDADR: UN 2811
WGK Germany: 3
RTECS: AU7358610
F: 10-21
HS Code: 29349990

Specification

 Cordycepin , with CAS number of 73-03-0, can be called 9H-Purin-6-amine, 9-(3-deoxy-.beta.-D-erythro-pentofuranosyl)- ; 9H-Purine, 6-amino-9-(3-deoxy-.beta.-D-ribofuranosyl)- ; Cordycepin ; 2'-Hydroxy-3'-deoxyadenosine erythro ; 3'-Deoxyadenosine . It is a crystalline solid. Cordycepin (CAS NO.73-03-0) is the first reported in nucleoside antibiotic.

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