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Tubercidin
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Name

Tubercidin

 EINECS 200-703-4
CAS No. 69-33-0 Density 1.9 g/cm3
PSA 126.65000 LogP -0.79380
Solubility N/A Melting Point 247-248 °C (decomp)(Solv: water (7732-18-5))
Formula C11H14 N4 O4 Boiling Point 648.8 °C at 760 mmHg
Molecular Weight 266.257 Flash Point 346.2 °C
Transport Information N/A Appearance N/A
Safety Poison by ingestion, intraperitoneal and intravenous routes. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. Risk Codes 28
Molecular Structure Molecular Structure of 69-33-0 (TUBERCIDIN) Hazard Symbols VeryT+
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

Article Data 16

Tubercidin Synthetic route

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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
nickel In N,N-dimethyl acetamide for 4h; Heating;67%
21193-80-6

5-Bromotubercidin

69-33-0

tubercidin

Conditions
ConditionsYield
With palladium on activated charcoal; ammonium formate In ethanol for 3h; Reflux;65%
24386-93-4

5-iodotubercidin

69-33-0

tubercidin

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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

Tubercidin Chemical Properties

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 Uses

  Tubercidin (CAS NO.69-33-0) is used as chemical reagent, fine chemicals, organic synthesis reagents, pharmaceutical intermediates.

Tubercidin 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.

Tubercidin 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  VeryT+
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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