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| CAS No.: | 69-33-0 |
|---|---|
| Name: | TUBERCIDIN |
| Molecular Structure: | |
|
|
|
| Formula: | C11H14 N4 O4 |
| Molecular Weight: | 266.257 |
| Synonyms: | 7H-Pyrrolo[2,3-d]pyrimidine,4-amino-7-b-D-ribofuranosyl- (7CI,8CI);Tubercidin (6CI); 4-Amino-7-(b-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine;6-Amino-9-D-ribofuranosyl-7-desazapurine; 7-Deazaadenosine; Adenosine,7-deaza-; Antibiotic XK 101-1; N7-Deazaadenosine; NSC 56408; Sparsamycin A;Sparsomycin A; Tubercidine; U 10071 |
| EINECS: | 200-703-4 |
| Density: | 1.9 g/cm3 |
| Melting Point: | 247-248 °C (decomp)(Solv: water (7732-18-5)) |
| Boiling Point: | 648.8 °C at 760 mmHg |
| Flash Point: | 346.2 °C |
| Hazard Symbols: |
 T+
|
| Risk Codes: | 28 |
| Safety: | Poison by ingestion, intraperitoneal and intravenous routes. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. |
| PSA: | 126.65000 |
| LogP: | -0.79380 |
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- 914458-26-7[5-(2-fluorophenyl)-1-pentyl-1H-pyrrol-3-yl]-1-naphthalenyl-Methanone
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- 71825-51-92-methyl-2-(4-nitrophenyl)propanenitrile
- 29914-75-8
(2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)tetrahydrofuran-3,4-diyl dibenzoate
- 69-33-0
tubercidin
| Conditions | Yield |
|---|---|
| With ammonia In methanol at 130℃; for 16h; | 85% |
- 16754-80-6
4-chloro-7-(β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidine
- 69-33-0
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; |
- 120401-34-5
4-(methylsulfonyl)-7-(β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidine
- 69-33-0
tubercidin
| Conditions | Yield |
|---|---|
| With ammonia In methanol at 50℃; for 12h; | 75% |
- 94773-30-5
4-Amino-2-(methylthio)-7-(β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin
- 69-33-0
tubercidin
| Conditions | Yield |
|---|---|
| nickel In N,N-dimethyl acetamide for 4h; Heating; | 67% |
- 21193-80-6
5-Bromotubercidin
- 69-33-0
tubercidin
| Conditions | Yield |
|---|---|
| With palladium on activated charcoal; ammonium formate In ethanol for 3h; Reflux; | 65% |
- 24386-93-4
5-iodotubercidin
- 69-33-0
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; |
- 85335-76-8
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
- 69-33-0
tubercidin
B
- 90813-69-7
2'-O-methylthiomethyltubercidin
C
- 64526-34-7
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 |
- 102690-94-8
2,3-O-isopropylidene-5-O-(tert-butyldimethylsilyl)-α-D-ribofuranosyl chloride
- 69-33-0
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 |
- 115479-39-5
4-chloro-7-<5-O-<(1,1-dimethylethyl)dimethylsilyl>-2,3-O-(1-methylethylidene)-β-D-ribofuranosyl>-7H-pyrrolo<2,3-d>pyrimidine
- 69-33-0
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 |
- 75921-20-9
5-O-<(1,1-dimethylethyl)dimethylsilyl>-2,3-O-(1-methylethylidene)-β-D-ribofuranose
- 69-33-0
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 |
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Chemistry
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
Uses
Tubercidin (CAS NO.69-33-0) is used as chemical reagent, fine chemicals, organic synthesis reagents, pharmaceutical intermediates.
Toxicity Data With Reference
| 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. |
Safety Profile
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