Cordycepin supplier | CasNO.73-03-0

Name
Cordycepin
EINECS 200-791-4
CAS No. 73-03-0
Article Data55
CAS DataBase
Density 1.91 g/cm³
Solubility
Melting Point 225-229 °C
Formula C₁₀H₁₃N₅O₃
Boiling Point 627.2 °C at 760 mmHg
Molecular Weight 251.245
Flash Point 333.1 °C
Transport Information UN 2811
Appearance crystalline solid
Safety 22-36-45-26
Risk Codes 40-36/37/38-25-20/21/22
Molecular Structure
Hazard Symbols Xn,T
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-;
PSA 119.31000
LogP -0.36960

Synthetic route

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

: 73-03-0
cordycepin

Conditions

Conditions	Yield
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

Conditions	Yield
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 sulfoxide	53%
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

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

: C14H16ClN5O5

: 73-03-0
cordycepin

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

: 54937-38-1
9-(3'-Deoxy-3'-iodo-β-D-xylofuranosyl)adenine

: 73-03-0
cordycepin

Conditions

Conditions	Yield
With 5% palladium on barium sulphate; hydrogen; triethylamine In methanol under 2280.15 Torr;	80%

: 2627-64-7, 4336-89-4, 40110-98-3
2',3'-dehydroadenosine

: 73-03-0
cordycepin

Conditions

Conditions	Yield
With lithium triethylborohydride In tetrahydrofuran; dimethyl sulfoxide at 4 - 20℃; for 17h; Inert atmosphere;	77%

: 6-heptanoylamido-9-(3-deoxy-2,5-di-O-benzoyl-β-D-erythropentofuranosyl)-purine

: 73-03-0
cordycepin

Conditions

Conditions	Yield
	75%

: C14H16BrN5O5

: 73-03-0
cordycepin

Conditions

Conditions	Yield
With formic acid; palladium 10% on activated carbon In methanol at 40℃; for 24h;	75%

: 3'-bromo-3'-deoxy-adenosine hydrochloride

: 73-03-0
cordycepin

Conditions

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen; sodium acetate In ethanol; water at 25℃; under 1551.49 Torr; for 44h; Inert atmosphere;	52.5%
Stage #1: 3'-bromo-3'-deoxy-adenosine hydrochloride With sodium acetate In ethanol; water for 1h; Stage #2: With hydrogen In ethanol; water at 20℃; under 760.051 - 1520.1 Torr; for 36h; Reagent/catalyst; Solvent;	100 g

: 2,2-Dimethyl-propionic acid 4-acetoxy-5-(6-benzoylamino-purin-9-yl)-tetrahydro-furan-2-ylmethyl ester

A: 73-03-0
cordycepin

B: cordycepin

Conditions

Conditions	Yield
With sodium methylate In methanol	A 42% B n/a

: 162825-78-7
2,2-Dimethyl-propionic acid (2S,4R,5R)-4-acetoxy-5-(6-benzoylamino-purin-9-yl)-tetrahydro-furan-2-ylmethyl ester

A: 73-03-0
cordycepin

B: 76902-49-3
N-(9-((2R,3R,5S)-3-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide

Conditions

Conditions	Yield
With sodium methylate In methanol at 20℃; for 20h;	A 42% B 16%

: 161001-78-1
2',5'-di-O-acetyl-3'-deoxy-N6-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine

A: 73-03-0
cordycepin

B: N6-carbamoyl-3'-deoxyadenosine

Conditions

Conditions	Yield
With ammonia for 18h; Ambient temperature;	A 25% B 41%

: 127246-65-5
2',3'-di-O-p-tolylsulphonyl-9-β-D-xylofuranosyladenine

A: 6998-75-0
3'-deoxydenosine

B: 73-03-0
cordycepin

Conditions

Conditions	Yield
With lithium triethylborohydride In tetrahydrofuran for 16h; Ambient temperature;	A 10% B 36%

: N-acetyl-2',5'-O-diacetyl-3'-iodo-3'-deoxyadenosine

A: 73-03-0
cordycepin

B: 4097-22-7
2',3'-Dideoxyadenosine

Conditions

Conditions	Yield
Stage #1: N-acetyl-2',5'-O-diacetyl-3'-iodo-3'-deoxyadenosine With lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile) In tetrahydrofuran; toluene for 12h; Reflux; Stage #2: With sodium methylate In methanol at 60℃; for 6h; Reagent/catalyst; Solvent;	A 31.3% B 4.8%

: N-acetyl-2',5'-O-diacetyl-3'-iodo-3'-deoxyadenosine

: 73-03-0
cordycepin

Conditions

Conditions	Yield
Stage #1: N-acetyl-2',5'-O-diacetyl-3'-iodo-3'-deoxyadenosine With lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile) In tetrahydrofuran; toluene for 4h; Reflux; Stage #2: With sodium methylate In methanol at 60℃; for 6h; Reagent/catalyst; Solvent;	30.2%

: 137530-37-1
9-(5-O-acetyl-3-deoxy-β-D-erythro-pentofuranosyl)adenine

: 73-03-0
cordycepin

Conditions

Conditions	Yield
With potassium hydroxide In acetone for 1h;	4 mg

: 112237-60-2
3'-deoxy-N6-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine

A: 73-03-0
cordycepin

B: N6-carbamoyl-3'-deoxyadenosine

Conditions

Conditions	Yield
With ammonia Ambient temperature;

: 157025-63-3
Benzoic acid (2S,4R,5R)-4-acetoxy-5-(6-benzoylamino-purin-9-yl)-tetrahydro-furan-2-ylmethyl ester

: 73-03-0
cordycepin

Conditions

Conditions	Yield
With MeOT; ammonia Ambient temperature; Yield given;

: 161001-78-1
2',5'-di-O-acetyl-3'-deoxy-N6-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine

A: 100-27-6
2-(4-nitrophenyl)ethanol

B: 73-03-0
cordycepin

C: 2-(4-nitrophenyl)ethyl carbamate

D: N6-carbamoyl-3'-deoxyadenosine

Conditions

Conditions	Yield
With ammonia for 18h; Product distribution; Mechanism; Ambient temperature;

...Expand

: 42867-78-7
9-(2'-O-Acetyl-3'-bromo-3'-deoxy-β-D-xylofuranosyl)adenine

A: 73-03-0
cordycepin

B: 4097-22-7
2',3'-Dideoxyadenosine

Conditions

Conditions	Yield
With sodium hydroxide; sodium acetate; palladium on activated charcoal 1.) CH3CN, RT, 6 h; Yield given. Multistep reaction. Yields of byproduct given;

: 37731-72-9
9-(2-O-acetyl-3-bromo-3-deoxy-5-O-(2,4,4-trimethyl-5-oxo-1,3-dioxolan-2-yl)-β-D-xylofuranosyl)adenine

A: 73-03-0
cordycepin

B: 4097-22-7
2',3'-Dideoxyadenosine

Conditions

Conditions	Yield
With sodium hydroxide; sodium acetate; palladium on activated charcoal 1.) CH3CN, RT, 3 h; Yield given. Multistep reaction. Yields of byproduct given;

: 134665-27-3
9-(5-O-acetyl-3-bromo-3-deoxy-β-D-xylofuranosyl)adenine

: 73-03-0
cordycepin

Conditions

Conditions	Yield
With sodium hydroxide; sodium carbonate; palladium on activated charcoal 1.) aq. CH3CN, RT, 24 h; Yield given. Multistep reaction;

: Acetic acid (2R,3S,4S,5R)-5-(6-amino-purin-9-yl)-3-bromo-4-methanesulfonyloxy-tetrahydro-furan-2-ylmethyl ester

A: 73-03-0
cordycepin

B: 4097-22-7
2',3'-Dideoxyadenosine

Conditions

Conditions	Yield
With sodium hydroxide; sodium carbonate; palladium on activated charcoal 1.) aq. CH3CN, RT, 2 h; Yield given. Multistep reaction. Yields of byproduct given;

: Pentanoic acid (2R,3S,4S,5R)-5-acetoxymethyl-2-(6-amino-purin-9-yl)-4-bromo-tetrahydro-furan-3-yl ester

A: 73-03-0
cordycepin

B: 4097-22-7
2',3'-Dideoxyadenosine

Conditions

Conditions	Yield
With sodium hydroxide; sodium acetate; palladium on activated charcoal 1.) CH3CN, RT, 11 h; Yield given. Multistep reaction. Yields of byproduct given;

: 73-03-0
cordycepin

: 108-24-7
acetic anhydride

: 71196-28-6
((2S,4R,5R)-4-acetoxy-5-(6-amino-9H-purin-9-yl)tetrahydrofuran-2-yl)methyl acetate

Conditions

Conditions	Yield
With pyridine; dmap for 4h; Ambient temperature;	100%
With pyridine at 20℃; for 0.5h;	82%

: 73-03-0
cordycepin

: 933-88-0
ortho-toluoyl chloride

: 3',5'-bis-O-o-toluoyl-6-N-O-o-toluoyl-3'-deoxyadenosine

Conditions

Conditions	Yield
With pyridine In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;	99%

: 73-03-0
cordycepin

: 13146-72-0
3’-deoxyinosine

Conditions

Conditions	Yield
With Azodicarboxamid In water at 50℃; for 1h; Deamination;	95%
With water at 37℃; for 1h; Enzymatic reaction;

: 73-03-0
cordycepin

: 58479-61-1
tert-butylchlorodiphenylsilane

: 862179-59-7
3'-deoxy-5'-O-[(tertbutyl)diphenylsilyl]adenosine

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 4h; Cooling;	92%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃;	90%
With pyridine at 40℃; for 6h;	85%

: 73-03-0
cordycepin

: 76-83-5
trityl chloride

: 90813-62-0
9-(3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)adenine

Conditions

Conditions	Yield
With pyridine at 50℃;	88%
In pyridine for 120h; Ambient temperature;	66%

: 73-03-0
cordycepin

: 98-88-4
benzoyl chloride

: 4395-38-4
N6,2',5'-tribenzoyl-3'-deoxyadenosine

Conditions

Conditions	Yield
With pyridine at 0℃; for 2.5h;	88%

: 73-03-0
cordycepin

: 98-88-4
benzoyl chloride

: 66884-45-5
(2R,3R,5S)-2-[6-(N-benzoylbenzamido)-9H-purin-9-yl]-5-[(benzoyloxy)methyl]oxolan-3-yl benzoate

Conditions

Conditions	Yield
With pyridine at 80℃; for 4h;	88%
In pyridine for 2h; Ambient temperature;	86%
With pyridine at 125℃; for 3h;	47%
In pyridine
With pyridine at 65℃; for 4h; Heating / reflux;

: 73-03-0
cordycepin

: 18162-48-6
tert-butyldimethylsilyl chloride

: 116285-72-4
9-((2R,3R,5S)-3-((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydrofuran-2-yl)-9H-purin-6-amine

Conditions

Conditions	Yield
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 0 - 23℃; for 10h; Inert atmosphere;	86%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃;	41%
With 1H-imidazole; dmap In N,N-dimethyl-formamide for 0.5h;
With 1H-imidazole; dmap In N,N-dimethyl-formamide for 0.5h;
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 16h;	1.56 g

: 108-05-4
vinyl acetate

: 73-03-0
cordycepin

: 137530-37-1
9-(5-O-acetyl-3-deoxy-β-D-erythro-pentofuranosyl)adenine

Conditions

Conditions	Yield
With CAL In tetrahydrofuran at 60℃; for 0.5h; Acetylation;	85%
With 1-butyl-3-methylimidazolium Tetrafluoroborate at 50℃; for 6h; Sonication; Enzymatic reaction; regioselective reaction;

: 73-03-0
cordycepin

: 57274-15-4
(2R,3R,5S)-2-(6-amino-9H-purin-9-yl)-5-(chloromethyl)tetrahydrofuran-3-ol

Conditions

Conditions	Yield
With thionyl chloride In N,N,N,N,N,N-hexamethylphosphoric triamide for 6h;	80%
With pyridine; thionyl chloride In acetonitrile at 0 - 20℃; for 19h;	61%
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; thionyl chloride at 0℃; for 7h;

: 73-03-0
cordycepin

: 79-03-8
propionyl chloride

: 77378-04-2
N-propionyl-cordycepin

Conditions

Conditions	Yield
With pyridine at 60℃; Inert atmosphere; Reflux;	75.5%

: 73-03-0
cordycepin

: 14470-28-1
mono-4-methoxytrityl chloride

: 51763-58-7
9-<5-O-(monomethoxytrityl)-3-deoxy-β-D-erythro-pentofuranosyl>adenine

Conditions

Conditions	Yield
With pyridine at 50℃; for 5h;	74%

: 40615-36-9
4,4'-dimethoxytrityl chloride

: 73-03-0
cordycepin

: 98-88-4
benzoyl chloride

: 84138-86-3
N-(9-((2R,3R,5S)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3-hydroxytetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide

Conditions

Conditions	Yield
Stage #1: 4,4'-dimethoxytrityl chloride; cordycepin With pyridine; N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 20℃; for 3h; Stage #2: benzoyl chloride In pyridine	69%

...Expand

: 73-03-0
cordycepin

: 98-68-0
4-methoxy-phenyl-sulphonyl chloride

: purine-6-(4-methoxy-benzenesulfonamido)-9-N-(3'-deoxy)ribofuranoside

Conditions

Conditions	Yield
Stage #1: cordycepin With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 4-methoxy-phenyl-sulphonyl chloride In N,N-dimethyl-formamide	68.6%

: 73-03-0
cordycepin

: 67373-56-2
chlorodimethyl(1,1,2-trimethylpropyl)silane

: 153764-71-7
(2R,3R,5S)-2-(6-Amino-purin-9-yl)-5-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-tetrahydro-furan-3-ol

Conditions

Conditions	Yield
With pyridine for 20h; Ambient temperature;	68%

: 73-03-0
cordycepin

: 111-64-8
n-octanoic acid chloride

: 77378-05-3
3-deoxy-β-D-ribofuranosyl-N6-biotinyladenine

Conditions

Conditions	Yield
With pyridine at 60℃; Inert atmosphere; Reflux;	64.3%

Cordycepin Chemical Properties

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

Cordycepin 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.

Cordycepin Consensus Reports

EPA Genetic Toxicology Program.

Cordycepin Safety Profile

Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits toxic fumes of NO_x.
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

Cordycepin 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.

Product Name

Cordycepin

Synthetic route

Cordycepin Chemical Properties

Cordycepin Toxicity Data With Reference

Cordycepin Consensus Reports

Cordycepin Safety Profile

Cordycepin Specification

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