G
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal; palladium hydroxide - carbon In water; tert-butyl alcohol at 20℃; under 2068.59 Torr; for 20h; Hydrogenolysis; | 99% |
G
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal; palladium hydroxide - carbon In water; tert-butyl alcohol at 20℃; under 2068.59 Torr; for 20h; Hydrogenolysis; | 98% |
N-2-(ethoxycarbonyl)guanosine
G
Conditions | Yield |
---|---|
With pyridine; ammonium hydroxide at 45℃; for 48h; | 95% |
G
Conditions | Yield |
---|---|
With ammonia In methanol at 25 - 28℃; for 10h; | 90% |
Conditions | Yield |
---|---|
With methanol; water; triethylamine at 71℃; Microwave irradiation; | 89% |
2-bromo-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)hypoxanthine
G
Conditions | Yield |
---|---|
With ammonia In methanol at 120℃; | 80% |
With ammonium hydroxide at 150℃; for 3h; | 48% |
G
Conditions | Yield |
---|---|
With methanol; ammonia for 24h; Ambient temperature; | 80% |
2-(acetylamino)-6-(diphenylcarbamoyloxy)-9-(β-D-tri-O-acetylribofuranosyl)-9H-purine
G
Conditions | Yield |
---|---|
With ammonia In methanol; water at 60℃; | 75% |
With methanol; ammonia for 24h; Ambient temperature; | 75% |
2',1''-anhydro-5-<(1''-benzamido-1''-hydroxymethylene)amino>-1-(β-D-ribofuranosyl)imidazole-4-carboxamide
A
G
C
<15NH2>guanosine
Conditions | Yield |
---|---|
With (15N)-ammonium chloride In dimethyl sulfoxide at 100℃; for 240h; Yields of byproduct given; | A n/a B 75% C n/a |
With (15N)-ammonium chloride In dimethyl sulfoxide at 100℃; for 240h; Yield given. Yields of byproduct given; |
8-mercaptoguanosine
G
Conditions | Yield |
---|---|
With potassium bromide In water at 20℃; pH=7; Reagent/catalyst; Inert atmosphere; Irradiation; | 57.4% |
Multi-step reaction with 3 steps 1: dihydrogen peroxide; acetic acid / 48 h / 65 °C 2: lithium hydroxide; water-d2 / Sonication 3: 24 h / 50 °C View Scheme |
1-(β-D-ribofuranosyl)-5-(thiocarbamoyl)amino-1H-imidazole-4-carboxamide
G
Conditions | Yield |
---|---|
With sodium hydroxide; copper diacetate for 1.5h; Heating; | 53% |
Conditions | Yield |
---|---|
With acetic acid; sodium nitrite anschl. Erhitzen mit aethanol. NH3; |
Conditions | Yield |
---|---|
bei der Einwirkung von Purinnucleosid-Phosphorylase; |
Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2-acetylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester
G
Conditions | Yield |
---|---|
With ammonia In methanol for 42h; Ambient temperature; | |
Multi-step reaction with 2 steps 1: 77 percent / EtN(i-Pr)2 / pyridine / 1 h / Ambient temperature 2: 75 percent / NH3/MeOH / 24 h / Ambient temperature View Scheme |
N2-acetyl-9-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)guanine
G
Conditions | Yield |
---|---|
With ammonia In methanol for 42h; Ambient temperature; |
2-amino-6-benzyloxy-9-β-D-ribofuranosylpurine
A
7-benzylguanosine
B
8-benzylguanosine
C
N2-benzyl-2'-deoxyguanosine
D
G
Conditions | Yield |
---|---|
With hydrogen cation In methanol; water at 40℃; Rate constant; Mechanism; pH 3.5, MeOH/aqueous buffer (5:95); other pH; | A 0.4 % Chromat. B 0.5 % Chromat. C 1.2 % Chromat. D 97.9 % Chromat. |
O6-(p-methylbenzyl)guanosine
A
1-(p-methylbenzyl)guanosine
B
N2-(p-methylbenzyl)guanosine
C
8-(p-methylbenzyl)guanosine
D
C18H21N5O5
E
G
Conditions | Yield |
---|---|
With hydrogen cation In methanol; water at 40℃; Rate constant; Mechanism; pH 3.5, MeOH/aqueous buffer (5:95); other pH; | A 1.2 % Chromat. B 3.9 % Chromat. C 2.6 % Chromat. D 2.9 % Chromat. E 89.4 % Chromat. |
O6-(p-chlorobenzyl)guanosine
G
Conditions | Yield |
---|---|
With hydrogen cation In methanol; water at 40℃; for 336h; Rate constant; Mechanism; pH 3.5, MeOH/aqueous buffer (5:95); other pH; | 100 % Chromat. |
O6-(p-methoxybenzyl)guanosine
A
N2-(p-methoxybenzyl)guanosine
B
1-(p-methoxybenzyl)guanosine
C
8-(p-methoxybenzyl)guanosine
D
7-(p-methoxybenzyl)guanosine
E
G
Conditions | Yield |
---|---|
With hydrogen cation In methanol; water at 40℃; Rate constant; Mechanism; pH 3.5, MeOH/aqueous buffer (5:95); other pH; | A 21.5 % Chromat. B 0.2 % Chromat. C 0.4 % Chromat. D 1.1 % Chromat. E 76.8 % Chromat. |
O6-(p-methoxybenzyl)guanosine
A
N2-(p-methoxybenzyl)guanosine
B
1-(p-methoxybenzyl)guanosine
C
8-(p-methoxybenzyl)guanosine
D
7-(p-methoxybenzyl)guanosine
E
4-(p-methoxybenzyl)-5-guanidino-1-β-D-ribofuranozylimidazole
F
G
Conditions | Yield |
---|---|
In methanol; water at 40℃; Rate constant; approximate rate constants for formation of products; |
Conditions | Yield |
---|---|
With ribonuclease A Product distribution; determination of structure; |
2'-O-(4-methoxytetrahydropyran-4-yl)guanosine
G
Conditions | Yield |
---|---|
With hydrogenchloride at 22℃; for 0.583333h; Kinetics; | 50 % Chromat. |
3-(β-D-pentofuranosyl)pyrimido<1,2-a>purin-10(3H)-one
A
Malondialdehyde
B
G
Conditions | Yield |
---|---|
With sodium hydroxide; water at 45℃; |
8-amino-3,10-dihydro-10-oxo-3-β-D-ribofuranosyl-1,3,5-triazino<1,2-a>purine
G
Conditions | Yield |
---|---|
With sodium hydroxide at 20℃; for 0.0833333h; Product distribution; |
N2-<<9-fluorenylmethyl)oxy>carbonyl>guanosine
G
Conditions | Yield |
---|---|
With ammonium hydroxide In pyridine at 20℃; for 0.5h; |
Conditions | Yield |
---|---|
In methanol; dimethyl sulfoxide at -26.1 - 29.9℃; Equilibrium constant; |
Conditions | Yield |
---|---|
With ribonuclease A Product distribution; determination of structure; |
Conditions | Yield |
---|---|
With water at 30℃; for 0.166667h; Rate constant; relative rate, different alkaline phosphotases; | |
In water at 37℃; for 240h; |
guanosine 2',3'-cyclic monophosphate
A
guanosine 3'-monophosphate
B
guanosine 2'-monophosphate
C
G
Conditions | Yield |
---|---|
With chicken plasma membrane protein In water at 30℃; for 2h; Product distribution; other temperatures; |
Conditions | Yield |
---|---|
With Croatalus Adamanteus snake venom phosphodiesterase; MgCl2,tris-hydrochloride buffer; monoesterase In water at 37℃; for 18h; Product distribution; |
N,N-dimethyl-formamide dimethyl acetal
G
N2-(dimethylaminomethylene)guanosine
Conditions | Yield |
---|---|
In methanol Ambient temperature; | 100% |
In methanol at 20℃; for 72h; | 99% |
In methanol for 72h; | 99% |
Conditions | Yield |
---|---|
With bromine In water at 20℃; | 100% |
With bromine In water at 20℃; for 24h; | 99% |
With bromine In water | 93% |
G
C12H13N7
Conditions | Yield |
---|---|
In water-d2 | 100% |
Conditions | Yield |
---|---|
Stage #1: allyl bromide; G In dimethyl sulfoxide at 20℃; for 18h; Stage #2: With hydrogenchloride; water In dimethyl sulfoxide for 0.75h; Stage #3: With sodium hydroxide In methanol; water; dimethyl sulfoxide | 100% |
Stage #1: allyl bromide; G In dimethyl sulfoxide at 20℃; for 18h; Inert atmosphere; Stage #2: With hydrogenchloride In water; dimethyl sulfoxide for 1h; | 92.5% |
In dimethyl sulfoxide at 20℃; for 24h; Concentration; Inert atmosphere; Large scale; | 58.7% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid at 20℃; for 72h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With dmap; triethylamine In acetonitrile at 0 - 20℃; for 4h; | 99% |
With dmap; triethylamine In acetonitrile for 0.5h; Ambient temperature; | 98% |
With dmap; triethylamine In acetonitrile Heating; | 98% |
G
<8-2H>guanosine
Conditions | Yield |
---|---|
With hydrogen; water-d2; palladium on activated charcoal at 110℃; for 24h; | 99% |
With water-d2 for 15h; Heating; | 92% |
With water-d2; palladium on activated charcoal; hydrogen at 110℃; for 24h; | 92% |
G
Conditions | Yield |
---|---|
With silver nitrate In water byproducts: AgCl; Pt-complex and Ag-salt soln. heating at 70-80°C for 2 h, AgCl centrifugation off, org. compd. soln. addn., soln. heating at 70°C for 2 h, centrifugation; soln. freeze drying; | 99% |
2-Methylpropionic anhydride
G
N2-(2-methylpropanoyl)-2',3',5'-tris-O-(2-methylpropanoyl)guanosine
Conditions | Yield |
---|---|
In pyridine at 110℃; for 20h; | 98% |
With dmap In pyridine at 50℃; for 24h; |
5,6-dimethyl-1H-benzo[d]imida-zole
G
(β-D-ribofuranosyl)-5,6-dimethylbenzimidazole
Conditions | Yield |
---|---|
for 1.5h; purine nucleoside phosphorylase of whole cells of E. coli BMT 1D/1A; | 98% |
Conditions | Yield |
---|---|
Stage #1: G With pyridine; chloro-trimethyl-silane In dichloromethane for 2h; Stage #2: Phenoxyacetyl chloride In dichloromethane at 0℃; for 3h; Stage #3: With methanol In dichloromethane at 20℃; for 12h; | 98% |
With pyridine; chloro-trimethyl-silane; benzotriazol-1-ol 1.) 45 min, 2.) acetonitrile, 55 deg C, 5 h; Yield given. Multistep reaction; | |
Stage #1: G With pyridine; chloro-trimethyl-silane In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere; Stage #2: Phenoxyacetyl chloride In dichloromethane for 3h; Cooling with ice; | 150.2 g |
Conditions | Yield |
---|---|
With sulfuric acid In water at 90℃; for 1.5h; Reagent/catalyst; Temperature; Solvent; Large scale; | 98% |
With sodium dichromate In water at 24.85℃; Quantum yield; Further Variations:; Reagents; pH-values; Decomposition; Photolysis; | |
With Lupinus luteus guanosine-inosine nucleosidase Enzyme kinetics; |
Conditions | Yield |
---|---|
With perchloric acid at 20℃; for 1.16667h; | 98% |
With perchloric acid In water at 20℃; for 4h; | 94% |
Stage #1: G; acetone With perchloric acid at 20℃; for 1.16667h; Stage #2: With ammonia In water at 0℃; | 92% |
Conditions | Yield |
---|---|
Stage #1: G With pyridine; chloro-trimethyl-silane In dichloromethane for 2h; Stage #2: acetyl chloride In dichloromethane at 0℃; for 1.5h; Stage #3: With methanol In dichloromethane at 20℃; for 12h; | 98% |
Conditions | Yield |
---|---|
In methanol; ethanol; water soln. of sodium nicotinate (5 mmol) in H2O/EtOH (1/10 v/v) added dropwise to soln. of Cu complex (5 mmol) in H2O/MeOH (1/10 v/v); stirred (5 min); guanosine (5 mmol) in EtOH added; stirred (12 h); solid isolated by filtration; washed with Et2O; dried (room temp.); elem. anal.; | 98% |
Conditions | Yield |
---|---|
Stage #1: ethyl iodide; G In N,N-dimethyl acetamide at 20℃; for 24h; Stage #2: With hydrogenchloride for 1.5h; Heating; | 97% |
propionic acid anhydride
G
2',3',5'-tri-O-propionyl-N2-propionylguanosine
Conditions | Yield |
---|---|
With dmap In pyridine at 70℃; for 3h; | 96% |
Conditions | Yield |
---|---|
Stage #1: G; dimethyl sulfate In N,N-dimethyl acetamide at 20℃; for 6h; Stage #2: With hydrogenchloride for 1.5h; Heating; | 96% |
acetic anhydride
G
A
2,9-diacetylguanine
B
1,2,3,5-tetraacetylribose
Conditions | Yield |
---|---|
Stage #1: acetic anhydride; G at 136℃; for 1h; Stage #2: With trifluoroacetic acid at 60 - 100℃; | A 96% B 86% |
acetic anhydride
G
2-amino-6-hydroxyl-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)purine
Conditions | Yield |
---|---|
With dmap; triethylamine In acetonitrile at 20℃; for 0.5h; | 96% |
With dmap; triethylamine In acetonitrile at 20℃; for 0.666667h; | 96% |
tert-butyldimethylsilyl chloride
G
5'-O-tert-butyldimethylsilylguanosine
Conditions | Yield |
---|---|
With silver nitrate In tetrahydrofuran for 3h; Ambient temperature; | 95% |
silver nitrate In tetrahydrofuran for 1h; | 95% |
With dmap; triethylamine In dichloromethane; dimethyl sulfoxide at 20℃; for 24h; Inert atmosphere; | 87% |
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane
G
3',5'-O-1,1,3,3-tetraisopropyldisiloxan-1,3-diyl-guanosine
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide for 0.75h; Ambient temperature; | 95% |
With 1H-imidazole In pyridine; N,N-dimethyl-formamide for 4h; | 93% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere; Large scale; | 92% |
di-tert-butylsilyl bis(trifluoromethanesulfonate)
G
2-amino-9-((4aR,6R,7R,7aS)-2,2-di-tert-butyl-7-hydroxytetrahydro-4H-furo[3,2-d][1,3,2]dioxasilin-6-yl)-1,9-dihydro-6H-purin-6-one
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide | 95% |
With 2,6-dimethylpyridine In N,N-dimethyl-formamide at 0 - 20℃; for 1h; Inert atmosphere; | 95% |
In N,N-dimethyl-formamide at 0℃; Inert atmosphere; | 89% |
N,N-dimethyl-formamide dimethyl acetal
G
N2-[(dimethylamino)methylene]guanosine
Conditions | Yield |
---|---|
In methanol at 27℃; for 96h; | 95% |
Conditions | Yield |
---|---|
Stage #1: oxirane; G With acetic acid at 100℃; for 0.5h; Stage #2: With hydrogenchloride for 1.5h; Heating; | 95% |
Conditions | Yield |
---|---|
In water; acetone stirring (hot soln., 3 h), pptn.; centrifugation, washing (water, acetone), drying (air); elem. anal.; | 95% |
Conditions | Yield |
---|---|
Stage #1: ethyl iodide; G In N,N-dimethyl acetamide at 60℃; Inert atmosphere; Stage #2: With hydrogenchloride In N,N-dimethyl acetamide; water at 110℃; for 1h; Stage #3: With ammonia In N,N-dimethyl acetamide; water at 20℃; | 95% |
Stage #1: ethyl iodide; G In N,N-dimethyl acetamide at 60℃; Inert atmosphere; Stage #2: With hydrogenchloride In N,N-dimethyl acetamide; water at 110℃; for 1h; | 95% |
Reported in EPA TSCA Inventory.
The Guanosine, with the CAS registry number 118-00-3 and EINECS registry number 204-227-8, has the IUPAC name of 2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one. It belongs to the following product categories: Pharmaceutical Intermediates; Purine; API intermediates; Biochemistry; Nucleosides and their analogs; Nucleosides, Nucleotides & Related Reagents; Bases & Related Reagents. And the molecular formula of the chemical is C10H13N5O5.
The Guanosine is a purine nucleoside comprising guanine attached to a ribose (ribofuranose) ring via a -N9-glycosidic bond, and is required for an RNA splicing reaction in mRNA. What's more, it is always used in herpes treatment.
The physical properties of Guanosine are as followings: (1)# of Rule of 5 Violations: 2; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 1.284; (5)ACD/KOC (pH 7.4): 1.278; (6)#H bond acceptors: 10; (7)#H bond donors: 6; (8)#Freely Rotating Bonds: 5; (9)Polar Surface Area: 155.22 Å2; (10)Index of Refraction: 1.955; (11)Molar Refractivity: 60.811 cm3; (12)Molar Volume: 125.448 cm3; (13)Polarizability: 24.107×10-24cm3; (14)Surface Tension: 123.824 dyne/cm; (15)Density: 2.258 g/cm3.
You should be cautious while dealing with this chemical. It is toxic if swallowed. Therefore, you had better take the following instructions: Avoid contact with skin and eyes; In case of accident or if you feel unwell, seek medical advice immediately (show label where possible); Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer).
You can still convert the following datas into molecular structure:
(1)SMILES: c1nc2c(=O)[nH]c(nc2n1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N
(2)InChI: InChI=1/C10H13N5O5/c11-10-13-7-4(8(19)14-10)12-2-15(7)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6-,9-/m1/s1
(3)InChIKey: NYHBQMYGNKIUIF-UUOKFMHZBU
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 500mg/kg (500mg/kg) | National Technical Information Service. Vol. AD277-689, | |
mouse | LD50 | intravenous | 180mg/kg (180mg/kg) | U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#03206, |
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