(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-(benzyloxy)-5-(hydroxymethyl) tetrahydrofuran-3-ol
adenosine
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In ethanol at 50℃; | 100% |
Conditions | Yield |
---|---|
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
adenosine
Conditions | Yield |
---|---|
With ammonium fluoride In methanol at 60℃; for 3h; | 99% |
With ammonium fluoride In methanol at 60℃; for 3h; other silyl ethers; | 99% |
Conditions | Yield |
---|---|
In 1,4-dioxane for 1.5h; Product distribution; Mechanism; Ambient temperature; | A 93% B 99% |
5'-O-(p-methoxyphenyldiphenylmethyl)adenosine
adenosine
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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
adenosine
Conditions | Yield |
---|---|
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
adenosine
Conditions | Yield |
---|---|
With ammonium peroxydisulfate; phosphate buffer at 80℃; for 2h; | 95% |
5'-O-dimethoxytrityladenosine
adenosine
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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
adenosine
Conditions | Yield |
---|---|
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
adenosine
Conditions | Yield |
---|---|
With ammonium cerium(IV) nitrate; silica gel In dichloromethane at 25℃; for 2h; detritylation; | 92% |
adenosine 1-oxide
adenosine
Conditions | Yield |
---|---|
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
adenosine
Conditions | Yield |
---|---|
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
adenosine
Conditions | Yield |
---|---|
In 1,4-dioxane; water for 1.5h; UV-irradiation; | 90% |
Conditions | Yield |
---|---|
With ammonium peroxydisulfate; phosphate buffer at 80℃; for 2h; | 89% |
Conditions | Yield |
---|---|
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; |
adenosine
Conditions | Yield |
---|---|
With ammonia at 120 - 130℃; for 24h; | 87.2% |
Conditions | Yield |
---|---|
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
adenosine
Conditions | Yield |
---|---|
With sodium naphthalenide In tetrahydrofuran at -78℃; | 82% |
adenosine
Conditions | Yield |
---|---|
With ammonia In methanol at 24℃; for 16h; | 80.9% |
9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine-6-sulfonamide
adenosine
Conditions | Yield |
---|---|
With ammonia In methanol at -5℃; for 5h; | 80% |
Conditions | Yield |
---|---|
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
adenosine
Conditions | Yield |
---|---|
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. |
Conditions | Yield |
---|---|
With nitric acid In water at 50℃; for 1h; | 79% |
Conditions | Yield |
---|---|
With Selectfluor; riboflavin In water; acetonitrile for 7h; Inert atmosphere; UV-irradiation; | 78% |
Conditions | Yield |
---|---|
With Selectfluor; riboflavin In water; acetonitrile at 37℃; under 760.051 Torr; for 7h; Inert atmosphere; Irradiation; | A 17% B 78% |
Conditions | Yield |
---|---|
With methanol; water; triethylamine at 71℃; Microwave irradiation; | 75% |
Conditions | Yield |
---|---|
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
adenosine
6-N-2',3',5'-tri-O-tetraacetyladenosine
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
adenosine
Conditions | Yield |
---|---|
In water-d2 | 100% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
at 20℃; for 3h; | 100% |
2,2-dimethoxy-propane
acetone
adenosine
2',3'-isopropylidene adenosine
Conditions | Yield |
---|---|
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
adenosine
6-N-(N,N-dibutylformamidine)adenosine
Conditions | Yield |
---|---|
In methanol at 20℃; for 12h; | 100% |
Conditions | Yield |
---|---|
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
adenosine
(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-((tert-butyldiphenylsilyloxy)methyl)tetrahydrofuran-3,4-diol
Conditions | Yield |
---|---|
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
adenosine
N6-(N,N'-Dimethylaminomethylene)adenosine
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 60℃; for 1h; | 99% |
In N,N-dimethyl-formamide at 40℃; for 1h; | 66% |
adenosine
[2,8-2H2]-adenosine
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
With copper(l) iodide; caesium carbonate; palladium diacetate In N,N-dimethyl-formamide at 120℃; for 13h; | 99% |
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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% |
adenosine
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
adenosine
N6,N6,2',3',5'-penta-O-toluoyladenosine
Conditions | Yield |
---|---|
In pyridine for 4h; Ambient temperature; | 98% |
Conditions | Yield |
---|---|
With pyridine; dmap for 2h; Ambient temperature; | 98% |
With dmap In various solvent(s) at 50℃; for 2.5h; | 92% |
adenosine
2',3'-dehydroadenosine
Conditions | Yield |
---|---|
With acetoxyisobutyryl bromide In water; acetonitrile at 20℃; for 1h; | 98% |
Ν,Ν-diisobutylformamide dimethylacetal
adenosine
Conditions | Yield |
---|---|
In methanol | 97.4% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With pyridine at 65℃; for 4h; | 96.2% |
In pyridine for 20h; | 94% |
With pyridine at 80℃; for 4h; | 82% |
Adenosine (CAS NO.58-61-7) is reported in EPA TSCA Inventory.
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. |
About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia
Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog
©2008 LookChem.com,License: ICP
NO.:Zhejiang16009103
complaints:service@lookchem.com Desktop View