(2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)tetrahydrofuran-3,4-diyl dibenzoate
tubercidin
Conditions | Yield |
---|---|
With ammonia In methanol at 130℃; for 16h; | 85% |
4-chloro-7-(β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidine
tubercidin
Conditions | Yield |
---|---|
With ammonia In methanol at 50℃; for 24h; | 82% |
With ammonia In methanol at 120℃; for 15h; | 81% |
With ammonia In methanol at 120 - 130℃; steel bomb, overnight; | 81% |
With ammonia In methanol at 120℃; Sealed tube; | 60.6% |
With ammonia In methanol at 110℃; for 16h; |
4-(methylsulfonyl)-7-(β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidine
tubercidin
Conditions | Yield |
---|---|
With ammonia In methanol at 50℃; for 12h; | 75% |
4-Amino-2-(methylthio)-7-(β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin
tubercidin
Conditions | Yield |
---|---|
nickel In N,N-dimethyl acetamide for 4h; Heating; | 67% |
5-Bromotubercidin
tubercidin
Conditions | Yield |
---|---|
With palladium on activated charcoal; ammonium formate In ethanol for 3h; Reflux; | 65% |
5-iodotubercidin
tubercidin
Conditions | Yield |
---|---|
With palladium on activated charcoal; ammonium formate In ethanol for 5h; Reflux; | 45% |
With palladium on activated charcoal; hydrogen; triethylamine In N,N-dimethyl-formamide for 18h; |
7-[3,5-O-[1,1,3,3-tetrakis(1-methylethyl)-1,3-disiloxanediyl]-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine
A
tubercidin
B
2'-O-methylthiomethyltubercidin
C
4-amino-7-(β-D-arabinofuranosyl)pyrrolo<2,3-d>pyrimidine
Conditions | Yield |
---|---|
With sodium tetrahydroborate; acetic anhydride 1.) DMSO, r.t., 27 h; 2.) EtOH, cooling to 0 deg C, 1 h; | A 12% B 7% C n/a |
2,3-O-isopropylidene-5-O-(tert-butyldimethylsilyl)-α-D-ribofuranosyl chloride
tubercidin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 65 percent / KOH / tris<2-(2-methoxyethoxy)ethyl>amine / tetrahydrofuran 2: 68 percent / 10percent aq.CF3COOH 3: 81 percent / 80percent 3-chloroperbenzoic acid / methanol / 2 h / Ambient temperature 4: 75 percent / NH3 / methanol / 12 h / 50 °C View Scheme | |
Multi-step reaction with 3 steps 1: 65 percent / KOH / tris<2-(2-methoxyethoxy)ethyl>amine / acetonitrile; tetrahydrofuran / 20 h 2: 89 percent / 90percent aq.CF3COOH / 1 h / Ambient temperature 3: 82 percent / NH3 / methanol / 24 h / 50 °C View Scheme | |
Multi-step reaction with 3 steps 1: 1) sodium hydride (60percent in oil) / 1) acetonitrile, 0.5 h; 2) THF, RT, overnight 2: 99 percent / trifluoroacetic acid / H2O / 1 h / Ambient temperature 3: 81 percent / NH3 / methanol / 120 - 130 °C / steel bomb, overnight View Scheme | |
Multi-step reaction with 3 steps 1: 67 percent / sodium hydride / acetonitrile / 1 h / Ambient temperature 2: 98.5 percent / aq. trifluoroacetic acid / 1 h / Ambient temperature 3: 81 percent / ammonia / methanol / 15 h / 120 °C View Scheme |
4-chloro-7-<5-O-<(1,1-dimethylethyl)dimethylsilyl>-2,3-O-(1-methylethylidene)-β-D-ribofuranosyl>-7H-pyrrolo<2,3-d>pyrimidine
tubercidin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 89 percent / 90percent aq.CF3COOH / 1 h / Ambient temperature 2: 82 percent / NH3 / methanol / 24 h / 50 °C View Scheme | |
Multi-step reaction with 2 steps 1: 99 percent / trifluoroacetic acid / H2O / 1 h / Ambient temperature 2: 81 percent / NH3 / methanol / 120 - 130 °C / steel bomb, overnight View Scheme | |
Multi-step reaction with 2 steps 1: 98.5 percent / aq. trifluoroacetic acid / 1 h / Ambient temperature 2: 81 percent / ammonia / methanol / 15 h / 120 °C View Scheme |
5-O-<(1,1-dimethylethyl)dimethylsilyl>-2,3-O-(1-methylethylidene)-β-D-ribofuranose
tubercidin
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: CCl4, tris(dimethylamino)phosphane / tetrahydrofuran / 2 h / -78 °C 2: 65 percent / KOH / tris<2-(2-methoxyethoxy)ethyl>amine / tetrahydrofuran 3: 68 percent / 10percent aq.CF3COOH 4: 81 percent / 80percent 3-chloroperbenzoic acid / methanol / 2 h / Ambient temperature 5: 75 percent / NH3 / methanol / 12 h / 50 °C View Scheme | |
Multi-step reaction with 4 steps 1: CCl4, tris(dimethylamino)phosphane / tetrahydrofuran / 2 h / -78 °C 2: 65 percent / KOH / tris<2-(2-methoxyethoxy)ethyl>amine / acetonitrile; tetrahydrofuran / 20 h 3: 89 percent / 90percent aq.CF3COOH / 1 h / Ambient temperature 4: 82 percent / NH3 / methanol / 24 h / 50 °C View Scheme |
7-<5-O-<(1,1-dimethylethyl)dimethylsilyl>-2,3-O-(1-methylethylidene)-β-D-ribofuranosyl>-4-(methylthio)-7H-pyrrolo<2,3-d>pyrimidine
tubercidin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 68 percent / 10percent aq.CF3COOH 2: 81 percent / 80percent 3-chloroperbenzoic acid / methanol / 2 h / Ambient temperature 3: 75 percent / NH3 / methanol / 12 h / 50 °C View Scheme |
4-(methylthio)-7-(β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidine
tubercidin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 81 percent / 80percent 3-chloroperbenzoic acid / methanol / 2 h / Ambient temperature 2: 75 percent / NH3 / methanol / 12 h / 50 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1) sodium hydride (60percent in oil) / 1) acetonitrile, 0.5 h; 2) THF, RT, overnight 2: 99 percent / trifluoroacetic acid / H2O / 1 h / Ambient temperature 3: 81 percent / NH3 / methanol / 120 - 130 °C / steel bomb, overnight View Scheme | |
Multi-step reaction with 3 steps 1: 67 percent / sodium hydride / acetonitrile / 1 h / Ambient temperature 2: 98.5 percent / aq. trifluoroacetic acid / 1 h / Ambient temperature 3: 81 percent / ammonia / methanol / 15 h / 120 °C View Scheme |
4-chloro-2-(methylthio)-7-(β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidine
tubercidin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 74 percent / conc. aq. NH3 / methanol / 20 h / 120 °C 2: 67 percent / Raney-Ni / N,N-dimethyl-acetamide / 4 h / Heating View Scheme |
tubercidin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sodium hydride / acetonitrile; mineral oil / 0.5 h / 20 °C / Inert atmosphere 1.2: 40 h / 20 °C 2.1: trifluoroacetic acid / water / 1 h / 0 - 20 °C 3.1: ammonia / methanol / 120 °C / Sealed tube View Scheme |
tubercidin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sodium hydride / acetonitrile; mineral oil / 0.5 h / 20 °C / Inert atmosphere 1.2: 40 h / 20 °C 2.1: trifluoroacetic acid / water / 1 h / 0 - 20 °C 3.1: ammonia / methanol / 120 °C / Sealed tube View Scheme |
tubercidin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: trifluoroacetic acid / water / 1 h / 0 - 20 °C 2: ammonia / methanol / 120 °C / Sealed tube View Scheme |
tubercidin
4-amino-7-(2,3-anhydro-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine
Conditions | Yield |
---|---|
Stage #1: tubercidin With 2-acetoxy-2-methylpropanoyl chloride In water; acetonitrile at 20℃; for 0.75h; Stage #2: With Dowex 1 x 2 (OH-) In methanol at 20℃; for 2h; Further stages.; | 100% |
With Dowex 1 x 2 (OH(-)); acetoxyisobutyryl bromide; water 1.) MeCN, 19-22 deg C, 1 h, 2.) MeOH, 1 h; Yield given. Multistep reaction; |
tubercidin
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In methanol Ambient temperature; | 97% |
Conditions | Yield |
---|---|
With acetic acid; sodium nitrite at 60℃; for 12h; | 96% |
N,N'-bis(dimethylaminomethylene)hydrazine
tubercidin
7-(β-D-ribofuranosyl)-4-(1,2,4-triazol-4-yl)pyrrolo<2,3-d>pyrimidine
Conditions | Yield |
---|---|
With pyridine at 100℃; for 24h; | 95% |
Conditions | Yield |
---|---|
In DMF (N,N-dimethyl-formamide) at 50℃; for 20h; | 94% |
Conditions | Yield |
---|---|
With pyridine at 50℃; for 2h; | 91% |
Stage #1: tubercidin; acetic anhydride With pyridine at 20 - 60℃; Stage #2: With 1H-imidazole In ethanol at 20℃; for 8h; | 85% |
Conditions | Yield |
---|---|
With pyridine at 20℃; for 1h; | 89% |
With pyridine 1.) 0 deg C, 1 h, 2.) 25 deg C, 5 h; | 86% |
With pyridine at 0 - 20℃; for 21h; Inert atmosphere; | 86% |
tubercidin
2,2-dimethoxy-propane
((3aR,4R,6R,6aR)-6-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol
Conditions | Yield |
---|---|
With camphor-10-sulfonic acid In water; acetone at 20℃; for 16h; Inert atmosphere; | 88% |
With toluene-4-sulfonic acid In acetone for 2h; Reflux; | 47% |
With toluene-4-sulfonic acid |
tubercidin
N,N-dimethylformamide diethyl diacetal
4-<<(dimethylamino)methylidene>amino>-7-(β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidine
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 50℃; for 1h; | 85% |
tubercidin
(2R,3R,4S,5S)-2-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(chloromethyl)tetrahydrofuran-3,4-diol
Conditions | Yield |
---|---|
Stage #1: tubercidin With pyridine In acetonitrile at 0℃; for 0.166667h; Inert atmosphere; Stage #2: With thionyl chloride In acetonitrile at 0 - 20℃; Stage #3: With ammonium hydroxide In methanol for 0.5h; | 85% |
tubercidin
tert-butyldimethylsilyl chloride
2',3',5'-Tri-O-(tert-butyldimethylsilyl)tubercidin
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide for 18h; Ambient temperature; | 71% |
Conditions | Yield |
---|---|
In methanol under N2 to (Rh(CO)2Cl)2 in CH3OH was added tubercidine and at 20°C for 2 h stirred; solvent evapd. in high vac., to the remained oil ether added; it formed solid material; filtrated, washed with ether. dried; elem. anal.; | 70% |
Conditions | Yield |
---|---|
Stage #1: tubercidin With di(n-butyl)tin oxide In methanol for 0.75h; Heating; Stage #2: p-toluenesulfonyl chloride With triethylamine In methanol for 0.166667h; Further stages.; | 67% |
tubercidin
(S)-2-tert-Butoxycarbonylamino-4-((S)-3-tert-butoxycarbonylamino-3-ethoxycarbonyl-propyldisulfanyl)-butyric acid ethyl ester
Conditions | Yield |
---|---|
With pyridine; triethylphosphine for 120h; Ambient temperature; | 66% |
tubercidin
(2S,2'S)-dimethyl 4,4'-disulfanediylbis(2-(2,2,2-trifluoroacetamido)butanoate)
(S)-4-[(2S,3S,4R,5R)-5-(4-Amino-pyrrolo[2,3-d]pyrimidin-7-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethylsulfanyl]-2-(2,2,2-trifluoro-acetylamino)-butyric acid methyl ester
Conditions | Yield |
---|---|
With tributylphosphine In pyridine for 96h; Ambient temperature; | 62% |
tubercidin
Conditions | Yield |
---|---|
With hydrogenchloride; [131I]-sodium iodide; N-chloro-4-methylbenzenesulfonamide; sodium hydroxide In ethanol; water at 20℃; for 0.05h; pH=7; | 61% |
tubercidin
trityl chloride
A
N6,5'-O-ditrityltubercidin
B
5'-O-trityltubercidin
Conditions | Yield |
---|---|
With pyridine for 48h; Ambient temperature; | A 22% B 57% |
tubercidin
Conditions | Yield |
---|---|
With pyridine; triethylphosphine for 96h; Ambient temperature; | 55% |
Conditions | Yield |
---|---|
In N,N,N,N,N,N-hexamethylphosphoric triamide for 24h; Heating; | 54% |
tubercidin
(S)-4-[(S)-3-Ethoxycarbonyl-3-(2-methoxy-acetylamino)-propyldisulfanyl]-2-(2-methoxy-acetylamino)-butyric acid ethyl ester
Conditions | Yield |
---|---|
With pyridine; triethylphosphine for 60h; Ambient temperature; | 54% |
tubercidin
(S)-2-(2-Methoxy-acetylamino)-4-[(S)-3-(2-methoxy-acetylamino)-3-propoxycarbonyl-propyldisulfanyl]-butyric acid propyl ester
Conditions | Yield |
---|---|
With pyridine; triethylphosphine for 96h; Ambient temperature; | 54% |
tubercidin
(S)-4-[(S)-3-Isopropoxycarbonyl-3-(2-methoxy-acetylamino)-propyldisulfanyl]-2-(2-methoxy-acetylamino)-butyric acid isopropyl ester
Conditions | Yield |
---|---|
With pyridine; triethylphosphine for 96h; Ambient temperature; | 53% |
tubercidin
(S)-4-[(S)-3-Ethoxycarbonyl-3-(2,2,2-trifluoro-acetylamino)-propyldisulfanyl]-2-(2,2,2-trifluoro-acetylamino)-butyric acid ethyl ester
Conditions | Yield |
---|---|
With pyridine; triethylphosphine for 70h; Ambient temperature; | 53% |
tubercidin
(S)-2-Acetylamino-4-((S)-3-acetylamino-3-propoxycarbonyl-propyldisulfanyl)-butyric acid propyl ester
Conditions | Yield |
---|---|
With pyridine; triethylphosphine for 96h; Ambient temperature; | 48% |
IUPAC Name: 2-(4-Aminopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)oxolane-3,4-diol
The MF of Tubercidin (CAS NO.69-33-0) is C11H14N4O4.
The MW of Tubercidin (CAS NO.69-33-0) is 266.25.
Synonyms of Tubercidin (CAS NO.69-33-0): 4-Amino-7-b-D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidine ; 7H-Pyrrolo(2,3-d)pyrimidin-4-amine, 7-beta-D-ribofuranosyl-
Index of Refraction: 1.834
EINECS: 200-703-4
Density: 1.9 g/ml
Flash Point: 346.2 °C
Boiling Point: 648.8 °C
Merck: 13,9875
Tubercidin (CAS NO.69-33-0) is used as chemical reagent, fine chemicals, organic synthesis reagents, pharmaceutical intermediates.
1. | dlt-mus-ipr 500 µg/kg | MUREAV Mutation Research. 54 (1978),226. | ||
2. | orl-rat LD50:16 mg/kg | CNREA8 Cancer Research. 29 (1969),116. | ||
3. | ipr-rat LD50:1 mg/kg | CNREA8 Cancer Research. 29 (1969),116. | ||
4. | orl-mus LD50:28,320 µg/kg | NCISP* National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program, Bethesda, MD 20205 JAN86 . | ||
5. | ipr-mus LD50:6 mg/kg | UPJOH* Compounds Available for Fundamental Research, Volume II-6, Antibiotics, A Program of Upjohn Company Research Laboratory .(Kalamazoo, MI.: )1971,2(6). | ||
6. | ivn-mus LD50:45 mg/kg | JAJAAA Journal of Antibiotics, Series A. 10 (1957),201. | ||
7. | orl-dog LDLo:48 mg/kg | CNREA8 Cancer Research. 29 (1969),116. | ||
8. | ivn-dog LDLo:48 mg/kg | CNREA8 Cancer Research. 29 (1969),116. |
Poison by ingestion, intraperitoneal and intravenous routes. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.Safety information of Tubercidin (CAS NO.69-33-0):
Hazard Codes T+
Risk Statements
28 Very Toxic if swallowed
Safety Statements
36/37/39 Wear suitable protective clothing, gloves and eye/face protection
45 In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
RIDADR UN 3462 6.1/PG 2
WGK Germany 3
RTECS UY8870000
F 10
HazardClass 6.1(a)
PackingGroup II
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