Product Name

  • Name

    Adenosine

  • EINECS 200-389-9
  • CAS No. 58-61-7
  • Article Data329
  • CAS DataBase
  • Density 2.08 g/cm3
  • Solubility Soluble in water, ammonium hydroxide and dimethyl sulfoxide. Insoluble in ethanol.
  • Melting Point 234-236 °C(lit.)
  • Formula C10H13N5O4
  • Boiling Point 676.3 °C at 760 mmHg
  • Molecular Weight 267.244
  • Flash Point 362.8 °C
  • Transport Information
  • Appearance white crystalline powder
  • Safety 24/25
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 58-61-7 (Adenosine)
  • Hazard Symbols
  • Synonyms Adenosine(AR);Adenocor;9-beta-D-Ribofuranosyl-9H-purin-6-amine;(3R,4R,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol;9H-Purin-6-amine, 9beta-D-ribofuranosyl-;Sandesin;Usaf cb-10;Myocol;.beta.-Adenosine;Adenosin [German];Boniton;Adenoside;9-β-D-Ribofuranosyladenine;.beta.-D-Ribofuranoside, adenine-9;.beta.-D-Adenosine;Adenocard;46969-16-8;beta-Adenosine;Adrekar;SR 96225;adenine-D-ribose;Adenosine [USAN:BAN];9.beta.-D-Ribofuranosyladenine;6-Amino-9.beta.-D-ribofuranosyl-9H-purine;adenine-9;Riboadenosine;D-Adenosine;Nucleocardyl;beta-D-Ribofuranose, 1-(6-amino-9H-purin-9-yl)-1-deoxy-;46946-45-6;Adenine nucleoside;(2R,3R,4R,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol;6-Amino-9-.beta.-ribofuranosyl-9H-purine;4-Aminopyrazolo[3,4-d]pyrimidine ribonucleoside;9-beta-D-Ribofuranosyladenine;Adenosine (8CI,9CI);Adenine riboside;
  • PSA 139.54000
  • LogP -1.39880

Synthetic route

(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-(benzyloxy)-5-(hydroxymethyl) tetrahydrofuran-3-ol
35638-82-5

(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-(benzyloxy)-5-(hydroxymethyl) tetrahydrofuran-3-ol

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol at 50℃;100%
triacetyladenosine
7387-57-7

triacetyladenosine

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
With lipase A from Aspergillus niger In aq. phosphate buffer; acetonitrile at 25℃; for 0.5h; pH=7; Enzymatic reaction;99%
With ammonia at 25℃;83%
With methanol; ammonia
3',5'-O-(1,1,3,3-tetra-isopropyldisiloxane-1,3-diyl)adenosine
69304-45-6

3',5'-O-(1,1,3,3-tetra-isopropyldisiloxane-1,3-diyl)adenosine

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
With ammonium fluoride In methanol at 60℃; for 3h;99%
With ammonium fluoride In methanol at 60℃; for 3h; other silyl ethers;99%
N6-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine
88121-73-7

N6-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine

methylamine
74-89-5

methylamine

A

2-(4-nitrophenyl)ethyl N-methylcarbamate

2-(4-nitrophenyl)ethyl N-methylcarbamate

B

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
In 1,4-dioxane for 1.5h; Product distribution; Mechanism; Ambient temperature;A 93%
B 99%
5'-O-(p-methoxyphenyldiphenylmethyl)adenosine
51600-11-4

5'-O-(p-methoxyphenyldiphenylmethyl)adenosine

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate; silica gel In dichloromethane at 25℃; for 0.1h; detritylation;98%
With hydrogenchloride In water; acetonitrile at 60℃; for 0.25h; pH=Ca. 1; Inert atmosphere;63 mg
N6-methyladenosine
1867-73-8

N6-methyladenosine

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
With benzophenone; Selectfluor In water; acetonitrile for 5h; Reagent/catalyst; Inert atmosphere; UV-irradiation;97%
With Selectfluor; riboflavin In water; acetonitrile at 37℃; under 760.051 Torr; for 2h; Reagent/catalyst; Inert atmosphere; Irradiation;86%
With manganese(IV) oxide; C17H20N4O9P(1-)*Na(1+); oxygen In water; acetonitrile at 20℃; under 760.051 Torr; for 7h; Mechanism; Kinetics; Reagent/catalyst; Irradiation; chemoselective reaction;79%
With dihydrogen peroxide; ammonium bicarbonate at 37℃; for 24h;
5'-O-(triphenylmethyl)adenosine
18048-85-6

5'-O-(triphenylmethyl)adenosine

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate; silica gel In dichloromethane at 25℃; for 1.5h; detritylation;95%
With cerium(IV) triflate; water In acetonitrile at 25℃; for 1.5h;88%
With chlorine In chloroform at 4℃; for 0.5h;85%
With sulfuric acid; water; silica gel In acetonitrile at 25℃; for 0.283333h;82%
With trifluoroacetic acid In water; acetonitrile at 0 - 20℃; for 12h;36 mg
(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-((4-methoxybenzyl)amino)-9H-purin-9-yl)tetrahydrofuran-3,4-diol
23666-24-2

(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-((4-methoxybenzyl)amino)-9H-purin-9-yl)tetrahydrofuran-3,4-diol

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
With ammonium peroxydisulfate; phosphate buffer at 80℃; for 2h;95%
5'-O-dimethoxytrityladenosine
57018-82-3, 81352-25-2

5'-O-dimethoxytrityladenosine

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
With K 10 clay In methanol; water for 20h; Ambient temperature;95%
With cerium(IV) triflate; water In acetonitrile at 25℃; for 0.75h;95%
With 1,1,1,3',3',3'-hexafluoro-propanol for 1h; Ambient temperature;87 % Turnov.
Multi-step reaction with 6 steps
1: Et3N; DMAP / CH2Cl2
2: dichloroacetic acid; pyrrole / CH2Cl2
3: 87 percent / 2,4,6-triisopropylbenzenesulfonyl chloride; 3-nitro-1,2,4-1H-triazole; pyridine / 1 h / 20 °C
4: Me3SiCl / acetonitrile / 6 h / 60 °C
5: 0.060 g / aq. NH3 / acetonitrile / 0.08 h / 20 °C
6: CD3CO2D; D2O / 23 °C
View Scheme
8-bromoadenosine
2946-39-6

8-bromoadenosine

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
With tris-(trimethylsilyl)silane; 2-hydroxyethanethiol In water at 100℃; for 4h;94%
With potassium fluoride; N,O-bis-(trimethylsilyl)-acetamide; perhydrodibenzo-18-crown-6 In acetonitrile for 96h; Heating;36%
With tris-(trimethylsilyl)silane; 2-hydroxyethanethiol; 1,1'-azobis(1-cyanocyclohexanenitrile); triethylamine In water at 100℃; for 1h;94 % Turnov.
Multi-step reaction with 2 steps
1.1: H2SO4; NaNO2; KBr / 3 h / -15 - 20 °C
1.2: H2O / 65 °C
1.3: 0.14 g / aq. NaOH / dimethylsulfoxide / 5 h
2.1: UV-irradiation
View Scheme
Multi-step reaction with 3 steps
1: pyridine / 0.5 h
2: sodium naphthalenide / tetrahydrofuran / -60 °C
3: aq. NH3 / methanol / 0.5 h
View Scheme
5'-(O-tert-butyldimethylsilyl)adenosine
69530-93-4

5'-(O-tert-butyldimethylsilyl)adenosine

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
With K 10 clay In methanol; water at 75℃; for 10h;93%
(2R,3R,4S,5R)-2-(6-(tritylamino)-9H-purin-9-yl)-5-((trityloxy)methyl)tetrahydrofuran-3,4-diol
31085-55-9

(2R,3R,4S,5R)-2-(6-(tritylamino)-9H-purin-9-yl)-5-((trityloxy)methyl)tetrahydrofuran-3,4-diol

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate; silica gel In dichloromethane at 25℃; for 2h; detritylation;92%
adenosine
58-61-7

adenosine

Conditions
ConditionsYield
With Dimethylphenylsilane In dimethyl sulfoxide at 20℃; for 24h; Inert atmosphere;91%
With GLUTATHIONE for 144h; Product distribution; Mechanism; Ambient temperature; Irradiation; pH 7.0 (phosphate buffer);60%
5'-(anthraquinon-2-ylmethoxycarbonyl)adenosine
350498-61-2

5'-(anthraquinon-2-ylmethoxycarbonyl)adenosine

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
With KMOPS buffer In tetrahydrofuran Photolysis;91%
[9-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-carbamic acid 2-nitro-benzyl ester
473910-22-4

[9-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-carbamic acid 2-nitro-benzyl ester

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
In 1,4-dioxane; water for 1.5h; UV-irradiation;90%
N6-Benzyladenosine
4294-16-0

N6-Benzyladenosine

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
With ammonium peroxydisulfate; phosphate buffer at 80℃; for 2h;89%
Conditions
ConditionsYield
With Enterobacter gergoviae CECT 875 in agarose In phosphate buffer at 60℃; for 3h; pH=7.0; Enzymatic reaction;89%
With Citrobacter koseri In aq. phosphate buffer at 60℃; for 1.5h; pH=7; Microbiological reaction;62%
With Escherichia coli BL21 In phosphate buffer at 60℃; for 1h; pH=7; Enzymatic reaction;
9-(2R,3R,4R,5R)-3,4-bis((tert-butyldiphenylsilyl)oxy)-5-((((tert-butyldiphenylsilyl)oxy)methyl)oxolan-2-yl)-6-chloro-9H-purine

9-(2R,3R,4R,5R)-3,4-bis((tert-butyldiphenylsilyl)oxy)-5-((((tert-butyldiphenylsilyl)oxy)methyl)oxolan-2-yl)-6-chloro-9H-purine

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
With ammonia at 120 - 130℃; for 24h;87.2%
Conditions
ConditionsYield
With Enterobacter gergoviae CECT 875 in agarose In phosphate buffer at 60℃; for 2h; pH=7.0; Enzymatic reaction;84%
With Escherichia coli BL21 In phosphate buffer at 60℃; pH=7; Enzymatic reaction;
2'-O-tosyladenosine
42776-78-3

2'-O-tosyladenosine

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
With sodium naphthalenide In tetrahydrofuran at -78℃;82%
C41H37N5O8Si

C41H37N5O8Si

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
With ammonia In methanol at 24℃; for 16h;80.9%
9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine-6-sulfonamide
123002-33-5

9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine-6-sulfonamide

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
With ammonia In methanol at -5℃; for 5h;80%
2',3'-isopropylidene adenosine
362-75-4

2',3'-isopropylidene adenosine

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
With K 10 clay In methanol; water at 75℃; for 55h;80%
With water at 150℃; for 0.5h; microwave irradiation;32%
Multi-step reaction with 3 steps
1.1: DMAP / CH2Cl2 / 17 h / 20 °C
1.2: CH2Cl2 / 48 h / 45 °C
2.1: 98 percent / TFA / tetrahydrofuran; H2O / 13 h
3.1: 91 percent / KMOPS buffer / tetrahydrofuran / Photolysis
View Scheme
With erbium(III) triflate In water at 120℃; for 0.5h; Microwave irradiation;88 % Chromat.
2-hydrazinoadenosine
15763-11-8

2-hydrazinoadenosine

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
With water; oxygen; copper(II) sulfate at 80℃; for 6h; Green chemistry;79%
With potassium trimethylsilonate In water at 70℃; for 48h; Temperature; Green chemistry;89 %Spectr.
8-mercaptoadenosine
3001-45-4

8-mercaptoadenosine

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
With nitric acid In water at 50℃; for 1h;79%
N,N-dimethyladenosine
2620-62-4

N,N-dimethyladenosine

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
With Selectfluor; riboflavin In water; acetonitrile for 7h; Inert atmosphere; UV-irradiation;78%
N,N-dimethyladenosine
2620-62-4

N,N-dimethyladenosine

A

N6-methyladenosine
1867-73-8

N6-methyladenosine

B

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
With Selectfluor; riboflavin In water; acetonitrile at 37℃; under 760.051 Torr; for 7h; Inert atmosphere; Irradiation;A 17%
B 78%
5'-O-acetyladenosine
2140-25-2

5'-O-acetyladenosine

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
With methanol; water; triethylamine at 71℃; Microwave irradiation;75%
N6,2',3',5'-tetra-O-benzoyladenosine
6984-53-8

N6,2',3',5'-tetra-O-benzoyladenosine

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
With ammonia In methanol at 50℃; for 16h;74%
With ammonia In methanol at 24℃; for 72h;62.7%
With ammonia In methanol Substitution;
acetic anhydride
108-24-7

acetic anhydride

adenosine
58-61-7

adenosine

6-N-2',3',5'-tri-O-tetraacetyladenosine
7387-58-8, 80007-24-5

6-N-2',3',5'-tri-O-tetraacetyladenosine

Conditions
ConditionsYield
With pyridine at 20℃;100%
In pyridine for 8h; Heating;55%
With sodium acetate
Stage #1: acetic anhydride; adenosine With pyridine at 20 - 60℃;
Stage #2: With 1H-imidazole; methanol at 20℃;
2.73 g
acetone
67-64-1

acetone

adenosine
58-61-7

adenosine

2',3'-isopropylidene adenosine
362-75-4

2',3'-isopropylidene adenosine

Conditions
ConditionsYield
With toluene-4-sulfonic acid; orthoformic acid triethyl ester at 20℃;100%
With p-toluenesulfonic acid monohydrate for 3h; Inert atmosphere;100%
With toluene-4-sulfonic acid at 20℃; for 1h; Inert atmosphere;99%
adenosine
58-61-7

adenosine

Inosine
58-63-9

Inosine

Conditions
ConditionsYield
With phosphate buffer at 25℃; for 0.666667h; AMP deaminase from Aspergillus sp.;100%
With calf intestine adenosine deaminase In water at 20℃; for 24h; Enzymatic reaction;100%
With water; adenosine deaminase for 16h; Enzymatic reaction;100%
C12H13N7
406945-71-9

C12H13N7

adenosine
58-61-7

adenosine

(2R,3R,4S,5R)-2-(6-Amino-purin-9-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-olate1-(2-amino-9H-purin-6-yl)-4-dimethylamino-pyridinium;

(2R,3R,4S,5R)-2-(6-Amino-purin-9-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-olate1-(2-amino-9H-purin-6-yl)-4-dimethylamino-pyridinium;

Conditions
ConditionsYield
In water-d2100%
adenosine
58-61-7

adenosine

5'-iodo-5'-deoxyadenosine
4099-81-4

5'-iodo-5'-deoxyadenosine

Conditions
ConditionsYield
With pyridine; iodine; triphenylphosphine at 20℃; for 2h;100%
With pyridine; iodine; triphenylphosphine for 2h;100%
With pyridine; iodine; triphenylphosphine at 0 - 20℃; for 2h;90%
3C5H13NO*3C9H9NO3

3C5H13NO*3C9H9NO3

adenosine
58-61-7

adenosine

3C5H13NO*3C9H9NO3*C10H13N5O4

3C5H13NO*3C9H9NO3*C10H13N5O4

Conditions
ConditionsYield
at 20℃; for 3h;100%
2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

acetone
67-64-1

acetone

adenosine
58-61-7

adenosine

2',3'-isopropylidene adenosine
362-75-4

2',3'-isopropylidene adenosine

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 20℃; for 72h; Inert atmosphere;100%
Stage #1: 2,2-dimethoxy-propane; acetone; adenosine With d-10-camphorsulphonic acid for 3h;
Stage #2: With sodium hydrogencarbonate In water; ethyl acetate
N,N-dibutylformamide dimethyl acetal
19449-30-0

N,N-dibutylformamide dimethyl acetal

adenosine
58-61-7

adenosine

6-N-(N,N-dibutylformamidine)adenosine
1228304-61-7

6-N-(N,N-dibutylformamidine)adenosine

Conditions
ConditionsYield
In methanol at 20℃; for 12h;100%
4-oxopentanoic acid ethyl ester
539-88-8

4-oxopentanoic acid ethyl ester

adenosine
58-61-7

adenosine

ethyl 3-[4-hydroxymethyl-2-methyl-6-(6-oxo-1,6-dihydropurin-9-yl)tetrahydrofuro[3,4-d][1,3]dioxol-2-yl]propionate

ethyl 3-[4-hydroxymethyl-2-methyl-6-(6-oxo-1,6-dihydropurin-9-yl)tetrahydrofuro[3,4-d][1,3]dioxol-2-yl]propionate

Conditions
ConditionsYield
Stage #1: 4-oxopentanoic acid ethyl ester; adenosine With hydrogenchloride; orthoformic acid triethyl ester In 1,4-dioxane; N,N-dimethyl-formamide at 20℃;
Stage #2: With calf intestine adenosine deaminase In water; glycerol at 20℃; for 72h; Enzymatic reaction;
100%
tert-butylchlorodiphenylsilane
58479-61-1

tert-butylchlorodiphenylsilane

adenosine
58-61-7

adenosine

(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-((tert-butyldiphenylsilyloxy)methyl)tetrahydrofuran-3,4-diol
119898-65-6

(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-((tert-butyldiphenylsilyloxy)methyl)tetrahydrofuran-3,4-diol

Conditions
ConditionsYield
With pyridine; dmap at 20℃; for 72h; Inert atmosphere;99%
With dmap In pyridine at 20℃; for 40h;98.9%
In pyridine for 24h; Ambient temperature;80%
N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

adenosine
58-61-7

adenosine

N6-(N,N'-Dimethylaminomethylene)adenosine
17331-15-6

N6-(N,N'-Dimethylaminomethylene)adenosine

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 60℃; for 1h;99%
In N,N-dimethyl-formamide at 40℃; for 1h;66%
adenosine
58-61-7

adenosine

[2,8-2H2]-adenosine
82845-88-3

[2,8-2H2]-adenosine

Conditions
ConditionsYield
With hydrogen; water-d2; palladium on activated charcoal at 110℃; for 24h;99%
With water-d2; palladium on activated charcoal; hydrogen at 110℃; for 24h;99%
With hydrogen; water-d2; palladium 10% on activated carbon at 110 - 140℃; for 48h; Product distribution / selectivity; Heating / reflux;74%
With deuterium In water-d2 at 55℃; under 1500.15 Torr; for 36h; Glovebox;
1-Iodonaphthalene
90-14-2

1-Iodonaphthalene

adenosine
58-61-7

adenosine

8-1-naphthyladenosine
1037298-62-6

8-1-naphthyladenosine

Conditions
ConditionsYield
With copper(l) iodide; caesium carbonate; palladium diacetate In N,N-dimethyl-formamide at 120℃; for 13h;99%
diphenyltin(IV) dichloride
1135-99-5

diphenyltin(IV) dichloride

adenosine
58-61-7

adenosine

A

[SnCl3(C6H5)(C5H2N4(C4H4O(OH)2CH2OH)NH2)2]

[SnCl3(C6H5)(C5H2N4(C4H4O(OH)2CH2OH)NH2)2]

B

triphenyltin chloride
639-58-7

triphenyltin chloride

Conditions
ConditionsYield
In methanol refluxing under N2 for 48 h;; removal of volatiles by distn.; residue was washed with ether in portions; ether extract afforded SnClPh3; elem. anal.;;A 99%
B n/a
Rh2(OCOCH3)2(NHCOCF3)2
499769-85-6

Rh2(OCOCH3)2(NHCOCF3)2

water
7732-18-5

water

adenosine
58-61-7

adenosine

[Rh2(acetato)2(trifluoroacetamido)2(adenosine)]*2H2O

[Rh2(acetato)2(trifluoroacetamido)2(adenosine)]*2H2O

Conditions
ConditionsYield
In methanol; water addn. of a hot (60°C) soln. of ligand in methanol to a soln. of rhodium complex in methanol at 60°C, standing at room temp.; filtration, air drying; elem. anal.;99%
tetrakis(μ-acetato)-dirhodium(II)*dimethanol

tetrakis(μ-acetato)-dirhodium(II)*dimethanol

adenosine
58-61-7

adenosine

tetrakis-μ-acetato-dirhodium(II) adenosine adduct

tetrakis-μ-acetato-dirhodium(II) adenosine adduct

Conditions
ConditionsYield
In methanol; water addn. of a hot (60°C) soln. of ligand in methanol to a soln. of rhodium complex in methanol at 60°C, standing at room temp.; filtration, air drying; elem. anal.;99%
methanol
67-56-1

methanol

tetrakis(μ-trifluoroacetamidato)dirhodium(II)
81988-04-7

tetrakis(μ-trifluoroacetamidato)dirhodium(II)

adenosine
58-61-7

adenosine

[Rh2(trifluoroacetamido)4(adenosine)]*2CH3OH

[Rh2(trifluoroacetamido)4(adenosine)]*2CH3OH

Conditions
ConditionsYield
In methanol; water addn. of a hot (60°C) soln. of ligand in methanol to a soln. of rhodium complex in methanol at 60°C, standing at room temp.; filtration, air drying; elem. anal.;99%
benzoyl chloride
98-88-4

benzoyl chloride

adenosine
58-61-7

adenosine

N6,N6,2'-O,3'-O-tetrabenzoyladenosine
58463-04-0

N6,N6,2'-O,3'-O-tetrabenzoyladenosine

Conditions
ConditionsYield
Stage #1: adenosine With pyridine; tert-butyldimethylsilyl chloride at 0 - 20℃; for 9h;
Stage #2: benzoyl chloride at 0 - 20℃;
Stage #3: With trifluoroacetic acid In tetrahydrofuran; water at 20℃; for 3h; Time;
99%
ortho-toluoyl chloride
933-88-0

ortho-toluoyl chloride

adenosine
58-61-7

adenosine

N6,N6,2',3',5'-penta-O-toluoyladenosine
104557-13-3

N6,N6,2',3',5'-penta-O-toluoyladenosine

Conditions
ConditionsYield
In pyridine for 4h; Ambient temperature;98%
benzoic acid anhydride
93-97-0

benzoic acid anhydride

adenosine
58-61-7

adenosine

2',3',5'-tri-O-benzoyladenosine
51549-15-6

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

Conditions
ConditionsYield
With pyridine; dmap for 2h; Ambient temperature;98%
With dmap In various solvent(s) at 50℃; for 2.5h;92%
adenosine
58-61-7

adenosine

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

2',3'-dehydroadenosine

Conditions
ConditionsYield
With acetoxyisobutyryl bromide In water; acetonitrile at 20℃; for 1h;98%
Ν,Ν-diisobutylformamide dimethylacetal
50746-36-6

Ν,Ν-diisobutylformamide dimethylacetal

adenosine
58-61-7

adenosine

N6-diisobutylaminomethyleneadenosine

N6-diisobutylaminomethyleneadenosine

Conditions
ConditionsYield
In methanol97.4%
2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

adenosine
58-61-7

adenosine

2',3'-isopropylidene adenosine
362-75-4

2',3'-isopropylidene adenosine

Conditions
ConditionsYield
With methanesulfonic acid In N,N-dimethyl-formamide; acetone at 60℃; for 6h; Inert atmosphere;96.3%
With Amberlyst 15H+ resin In DMF (N,N-dimethyl-formamide) at 55℃; for 3h;95%
With Amberlyst 15H+ resin In N,N-dimethyl-formamide at 55℃; for 3h;95%
benzoyl chloride
98-88-4

benzoyl chloride

adenosine
58-61-7

adenosine

N6,N6,2',3',5'-pentabenzoyl-β-D-adenosine
62374-23-6

N6,N6,2',3',5'-pentabenzoyl-β-D-adenosine

Conditions
ConditionsYield
With pyridine at 65℃; for 4h;96.2%
In pyridine for 20h;94%
With pyridine at 80℃; for 4h;82%

Adenosine Consensus Reports

  Adenosine (CAS NO.58-61-7) is reported in EPA TSCA Inventory.

Adenosine Specification

The Adenosine, with the CAS registry number 58-61-7, is also known as 9H-Purin-6-amine, 9beta-D-ribofuranosyl-. It belongs to the product categories of Pharmaceutical Intermediates; Fine Chemical & Intermediates; Purine; API intermediates; Nucleosides and their analogs; Biochemistry; Nucleosides, Nucleotides & Related Reagents; Nucleic acids. Its EINECS registry number is 200-389-9. This chemical's molecular formula is C10H13N5O4 and molecular weight is 267.24. Its IUPAC name is called (2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol. This chemical's classification codes are Analgesics; Anti-arrhythmia agents; Cardiac depressant [anti-arrhythmic]; Cardiovascular agents; Central Nervous System Agents; Drug / Therapeutic Agent; Human Data; Mutation data; Peripheral Nervous System Agents; Sensory System Agents; Vasodilator agents. When you are using this chemical, please be cautious about it. You must avoid contacting it with skin and eyes. 

Physical properties of Adenosine: (1)# of Rule of 5 Violations: 1; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 8.94; (5)ACD/KOC (pH 7.4): 9.254; (6)#H bond acceptors: 9; (7)#H bond donors: 5; (8)#Freely Rotating Bonds: 5; (9)Index of Refraction: 1.907; (10)Molar Refractivity: 59.959 cm3; (11)Molar Volume: 128.164 cm3; (12)Surface Tension: 107.624 dyne/cm; (13)Density: 2.085 g/cm3; (14)Flash Point: 362.796 °C; (15)Enthalpy of Vaporization: 104.298 kJ/mol; (16)Boiling Point: 676.271 °C at 760 mmHg; (17)Vapour Pressure: 0 mmHg at 25°C.

Preparation: Adenosine can be prepared by O2',O3',O5'-triacetyl-adenosine. This reaction will need reagent methanol and NH3.



Uses of Adenosine: it can be used to produce O2'-methyl-adenosine. This reaction will need reagent aqueous 1,2-dimethoxy-ethane.



Adenosine is a nucleoside composed of a molecule of adenine attached to a ribose sugar molecule (ribofuranose) moiety via a β-N9-glycosidic bond. Adenosine is an endogenous purine nucleoside that modulates many physiological processes. Adenosine plays an important role in biochemical processes, such as energy transfer—as adenosine triphosphate (ATP) and adenosine diphosphate (ADP)—as well as in signal transduction as cyclic adenosine monophosphate, cAMP.

You can still convert the following datas into molecular structure:
(1)SMILES:c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N;
(2)Std. InChI:InChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1;
(3)Std. InChIKey:OIRDTQYFTABQOQ-KQYNXXCUSA-N;

The toxicity data is of Adenosine as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo intravenous 50ug/kg/1M-I (0.05mg/kg) LUNGS, THORAX, OR RESPIRATION: BRONCHIOLAR CONSTRICTION Human & Experimental Toxicology. Vol. 13, Pg. 263, 1994.
man TDLo intravenous 143ug/kg/I (0.143mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BEHAVIORAL: HEADACHE
Medical Journal of Australia.
man TDLo intravenous 171ug/kg (0.171mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: COMA

CARDIAC: PULSE RATE
American Journal of Emergency Medicine. Vol. 11, Pg. 192, 1993.
man TDLo intravenous 257ug/kg (0.257mg/kg) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
American Journal of Emergency Medicine. Vol. 11, Pg. 249, 1993.
man TDLo intravenous 257ug/kg/1D-I (0.257mg/kg) CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

CARDIAC: CHANGE IN RATE
Annals of Internal Medicine. Vol. 122, Pg. 351, 1995.
mouse LD50 intraperitoneal 500mg/kg (500mg/kg)   National Technical Information Service. Vol. AD277-689,
mouse LD50 oral > 20gm/kg (20000mg/kg)   Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 45, 1980.
women TDLo intravenous 240ug/kg (0.24mg/kg) CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) American Journal of Emergency Medicine. Vol. 14, Pg. 300, 1996.
women TDLo intravenous 360ug/kg/1H-I (0.36mg/kg) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

CARDIAC: CHANGE IN RATE
American Journal of Emergency Medicine. Vol. 10, Pg. 326, 1992.

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