Product Name

  • Name

    TUBERCIDIN

  • EINECS 200-703-4
  • CAS No. 69-33-0
  • Article Data16
  • CAS DataBase
  • Density 1.9 g/cm3
  • Solubility
  • 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
  • Appearance
  • 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
  • PSA 126.65000
  • LogP -0.79380

Synthetic route

(2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)tetrahydrofuran-3,4-diyl dibenzoate
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

tubercidin
69-33-0

tubercidin

Conditions
ConditionsYield
With ammonia In methanol at 130℃; for 16h;85%
4-chloro-7-(β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidine
16754-80-6

4-chloro-7-(β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidine

tubercidin
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;
4-(methylsulfonyl)-7-(β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidine
120401-34-5

4-(methylsulfonyl)-7-(β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidine

tubercidin
69-33-0

tubercidin

Conditions
ConditionsYield
With ammonia In methanol at 50℃; for 12h;75%
4-Amino-2-(methylthio)-7-(β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin
94773-30-5

4-Amino-2-(methylthio)-7-(β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin

tubercidin
69-33-0

tubercidin

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

5-Bromotubercidin

tubercidin
69-33-0

tubercidin

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

5-iodotubercidin

tubercidin
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;
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
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

tubercidin
69-33-0

tubercidin

B

2'-O-methylthiomethyltubercidin
90813-69-7

2'-O-methylthiomethyltubercidin

C

4-amino-7-(β-D-arabinofuranosyl)pyrrolo<2,3-d>pyrimidine
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
2,3-O-isopropylidene-5-O-(tert-butyldimethylsilyl)-α-D-ribofuranosyl chloride
102690-94-8

2,3-O-isopropylidene-5-O-(tert-butyldimethylsilyl)-α-D-ribofuranosyl chloride

tubercidin
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
4-chloro-7-<5-O-<(1,1-dimethylethyl)dimethylsilyl>-2,3-O-(1-methylethylidene)-β-D-ribofuranosyl>-7H-pyrrolo<2,3-d>pyrimidine
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

tubercidin
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
5-O-<(1,1-dimethylethyl)dimethylsilyl>-2,3-O-(1-methylethylidene)-β-D-ribofuranose
75921-20-9

5-O-<(1,1-dimethylethyl)dimethylsilyl>-2,3-O-(1-methylethylidene)-β-D-ribofuranose

tubercidin
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
7-<5-O-<(1,1-dimethylethyl)dimethylsilyl>-2,3-O-(1-methylethylidene)-β-D-ribofuranosyl>-4-(methylthio)-7H-pyrrolo<2,3-d>pyrimidine
120401-29-8

7-<5-O-<(1,1-dimethylethyl)dimethylsilyl>-2,3-O-(1-methylethylidene)-β-D-ribofuranosyl>-4-(methylthio)-7H-pyrrolo<2,3-d>pyrimidine

tubercidin
69-33-0

tubercidin

Conditions
ConditionsYield
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
16754-86-2

4-(methylthio)-7-(β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidine

tubercidin
69-33-0

tubercidin

Conditions
ConditionsYield
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
4-chloro-1H-pyrrolo[2,3-d]pyrimidine
3680-69-1

4-chloro-1H-pyrrolo[2,3-d]pyrimidine

tubercidin
69-33-0

tubercidin

Conditions
ConditionsYield
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
85572-94-7

4-chloro-2-(methylthio)-7-(β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidine

tubercidin
69-33-0

tubercidin

Conditions
ConditionsYield
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
2,3-O-isopropylidene-5-O-(tertbutyldimethyl)-α-D-ribofuranosyl chloride

2,3-O-isopropylidene-5-O-(tertbutyldimethyl)-α-D-ribofuranosyl chloride

tubercidin
69-33-0

tubercidin

Conditions
ConditionsYield
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
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

4-chloro-1H-pyrrolo[2,3-d]pyrimidine

tubercidin
69-33-0

tubercidin

Conditions
ConditionsYield
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
4-chloro-2,3-O-isopropylidene-5-O-(tertbutyldimethylsilyl)-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

4-chloro-2,3-O-isopropylidene-5-O-(tertbutyldimethylsilyl)-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

tubercidin
69-33-0

tubercidin

Conditions
ConditionsYield
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
69-33-0

tubercidin

4-amino-7-(2,3-anhydro-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine
40627-31-4

4-amino-7-(2,3-anhydro-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine

Conditions
ConditionsYield
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
69-33-0

tubercidin

(2R,3R,4S,5R)-2-(4-Amino-3-oxy-pyrrolo[2,3-d]pyrimidin-7-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol

(2R,3R,4S,5R)-2-(4-Amino-3-oxy-pyrrolo[2,3-d]pyrimidin-7-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In methanol Ambient temperature;97%
tubercidin
69-33-0

tubercidin

7-β-D-ribofuranosylpyrrolo<2,3-d>pyrimidin-4-one
2862-16-0

7-β-D-ribofuranosylpyrrolo<2,3-d>pyrimidin-4-one

Conditions
ConditionsYield
With acetic acid; sodium nitrite at 60℃; for 12h;96%
N,N'-bis(dimethylaminomethylene)hydrazine
16114-05-9

N,N'-bis(dimethylaminomethylene)hydrazine

tubercidin
69-33-0

tubercidin

7-(β-D-ribofuranosyl)-4-(1,2,4-triazol-4-yl)pyrrolo<2,3-d>pyrimidine
163632-56-2

7-(β-D-ribofuranosyl)-4-(1,2,4-triazol-4-yl)pyrrolo<2,3-d>pyrimidine

Conditions
ConditionsYield
With pyridine at 100℃; for 24h;95%
2-chloroethanal
107-20-0

2-chloroethanal

tubercidin
69-33-0

tubercidin

N1-deazaethenoadenosine
53437-77-7

N1-deazaethenoadenosine

Conditions
ConditionsYield
In DMF (N,N-dimethyl-formamide) at 50℃; for 20h;94%
tubercidin
69-33-0

tubercidin

acetic anhydride
108-24-7

acetic anhydride

4-acetylamino-7-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

4-acetylamino-7-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

Conditions
ConditionsYield
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%
tubercidin
69-33-0

tubercidin

acetic anhydride
108-24-7

acetic anhydride

2',3',5'-tri-O-acetyltubercidin
60343-84-2

2',3',5'-tri-O-acetyltubercidin

Conditions
ConditionsYield
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
69-33-0

tubercidin

2,2-dimethoxy-propane
77-76-9

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
16739-75-6

((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
ConditionsYield
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
69-33-0

tubercidin

N,N-dimethylformamide diethyl diacetal
1188-33-6

N,N-dimethylformamide diethyl diacetal

4-<<(dimethylamino)methylidene>amino>-7-(β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidine
57881-19-3

4-<<(dimethylamino)methylidene>amino>-7-(β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidine

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 50℃; for 1h;85%
tubercidin
69-33-0

tubercidin

(2R,3R,4S,5S)-2-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(chloromethyl)tetrahydrofuran-3,4-diol
53458-85-8

(2R,3R,4S,5S)-2-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(chloromethyl)tetrahydrofuran-3,4-diol

Conditions
ConditionsYield
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
69-33-0

tubercidin

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

2',3',5'-Tri-O-(tert-butyldimethylsilyl)tubercidin
87119-54-8

2',3',5'-Tri-O-(tert-butyldimethylsilyl)tubercidin

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide for 18h; Ambient temperature;71%
di(rhodium)tetracarbonyl dichloride

di(rhodium)tetracarbonyl dichloride

tubercidin
69-33-0

tubercidin

dicarbonylchloro(7-desazaadenosin)rhodium(I)

dicarbonylchloro(7-desazaadenosin)rhodium(I)

Conditions
ConditionsYield
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%
tubercidin
69-33-0

tubercidin

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

2'-O-tosyltubercidin

2'-O-tosyltubercidin

Conditions
ConditionsYield
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
69-33-0

tubercidin

(S)-2-tert-Butoxycarbonylamino-4-((S)-3-tert-butoxycarbonylamino-3-ethoxycarbonyl-propyldisulfanyl)-butyric acid ethyl ester
144385-04-6

(S)-2-tert-Butoxycarbonylamino-4-((S)-3-tert-butoxycarbonylamino-3-ethoxycarbonyl-propyldisulfanyl)-butyric acid ethyl ester

(S)-4-[(2S,3S,4R,5R)-5-(4-Amino-pyrrolo[2,3-d]pyrimidin-7-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethylsulfanyl]-2-tert-butoxycarbonylamino-butyric acid ethyl ester

(S)-4-[(2S,3S,4R,5R)-5-(4-Amino-pyrrolo[2,3-d]pyrimidin-7-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethylsulfanyl]-2-tert-butoxycarbonylamino-butyric acid ethyl ester

Conditions
ConditionsYield
With pyridine; triethylphosphine for 120h; Ambient temperature;66%
tubercidin
69-33-0

tubercidin

(2S,2'S)-dimethyl 4,4'-disulfanediylbis(2-(2,2,2-trifluoroacetamido)butanoate)
84355-09-9

(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
100804-03-3

(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
ConditionsYield
With tributylphosphine In pyridine for 96h; Ambient temperature;62%
tubercidin
69-33-0

tubercidin

5-[131I]iodotubercidin

5-[131I]iodotubercidin

Conditions
ConditionsYield
With hydrogenchloride; [131I]-sodium iodide; N-chloro-4-methylbenzenesulfonamide; sodium hydroxide In ethanol; water at 20℃; for 0.05h; pH=7;61%
tubercidin
69-33-0

tubercidin

trityl chloride
76-83-5

trityl chloride

A

N6,5'-O-ditrityltubercidin
112135-89-4

N6,5'-O-ditrityltubercidin

B

5'-O-trityltubercidin
40983-03-7

5'-O-trityltubercidin

Conditions
ConditionsYield
With pyridine for 48h; Ambient temperature;A 22%
B 57%
tubercidin
69-33-0

tubercidin

(S)-2-Acetylamino-4-((S)-3-acetylamino-3-isopropoxycarbonyl-propyldisulfanyl)-butyric acid isopropyl ester

(S)-2-Acetylamino-4-((S)-3-acetylamino-3-isopropoxycarbonyl-propyldisulfanyl)-butyric acid isopropyl ester

(S)-2-Acetylamino-4-[(2S,3S,4R,5R)-5-(4-amino-pyrrolo[2,3-d]pyrimidin-7-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethylsulfanyl]-butyric acid isopropyl ester

(S)-2-Acetylamino-4-[(2S,3S,4R,5R)-5-(4-amino-pyrrolo[2,3-d]pyrimidin-7-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethylsulfanyl]-butyric acid isopropyl ester

Conditions
ConditionsYield
With pyridine; triethylphosphine for 96h; Ambient temperature;55%
tubercidin
69-33-0

tubercidin

prenyl bromide
870-63-3

prenyl bromide

N4-(Δ2-Isopentenyl)tubercidin
23589-13-1

N4-(Δ2-Isopentenyl)tubercidin

Conditions
ConditionsYield
In N,N,N,N,N,N-hexamethylphosphoric triamide for 24h; Heating;54%
tubercidin
69-33-0

tubercidin

(S)-4-[(S)-3-Ethoxycarbonyl-3-(2-methoxy-acetylamino)-propyldisulfanyl]-2-(2-methoxy-acetylamino)-butyric acid ethyl ester
144373-81-9

(S)-4-[(S)-3-Ethoxycarbonyl-3-(2-methoxy-acetylamino)-propyldisulfanyl]-2-(2-methoxy-acetylamino)-butyric acid ethyl ester

N-(methoxyacetyl)-S-tubercidinyl-L-homocysteine ethyl ester

N-(methoxyacetyl)-S-tubercidinyl-L-homocysteine ethyl ester

Conditions
ConditionsYield
With pyridine; triethylphosphine for 60h; Ambient temperature;54%
tubercidin
69-33-0

tubercidin

(S)-2-(2-Methoxy-acetylamino)-4-[(S)-3-(2-methoxy-acetylamino)-3-propoxycarbonyl-propyldisulfanyl]-butyric acid propyl ester
144373-82-0

(S)-2-(2-Methoxy-acetylamino)-4-[(S)-3-(2-methoxy-acetylamino)-3-propoxycarbonyl-propyldisulfanyl]-butyric acid propyl ester

N-(methoxyacetyl)-S-tubercidinyl-L-homocysteine propyl ester

N-(methoxyacetyl)-S-tubercidinyl-L-homocysteine propyl ester

Conditions
ConditionsYield
With pyridine; triethylphosphine for 96h; Ambient temperature;54%
tubercidin
69-33-0

tubercidin

(S)-4-[(S)-3-Isopropoxycarbonyl-3-(2-methoxy-acetylamino)-propyldisulfanyl]-2-(2-methoxy-acetylamino)-butyric acid isopropyl ester
144373-83-1

(S)-4-[(S)-3-Isopropoxycarbonyl-3-(2-methoxy-acetylamino)-propyldisulfanyl]-2-(2-methoxy-acetylamino)-butyric acid isopropyl ester

(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-methoxy-acetylamino)-butyric acid isopropyl ester

(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-methoxy-acetylamino)-butyric acid isopropyl ester

Conditions
ConditionsYield
With pyridine; triethylphosphine for 96h; Ambient temperature;53%
tubercidin
69-33-0

tubercidin

(S)-4-[(S)-3-Ethoxycarbonyl-3-(2,2,2-trifluoro-acetylamino)-propyldisulfanyl]-2-(2,2,2-trifluoro-acetylamino)-butyric acid ethyl ester
144373-75-1

(S)-4-[(S)-3-Ethoxycarbonyl-3-(2,2,2-trifluoro-acetylamino)-propyldisulfanyl]-2-(2,2,2-trifluoro-acetylamino)-butyric acid ethyl ester

(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 ethyl ester

(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 ethyl ester

Conditions
ConditionsYield
With pyridine; triethylphosphine for 70h; Ambient temperature;53%
tubercidin
69-33-0

tubercidin

(S)-2-Acetylamino-4-((S)-3-acetylamino-3-propoxycarbonyl-propyldisulfanyl)-butyric acid propyl ester
144373-79-5

(S)-2-Acetylamino-4-((S)-3-acetylamino-3-propoxycarbonyl-propyldisulfanyl)-butyric acid propyl ester

N-acetyl-S-tubercidinyl-L-homocysteine propyl ester

N-acetyl-S-tubercidinyl-L-homocysteine propyl ester

Conditions
ConditionsYield
With pyridine; triethylphosphine for 96h; Ambient temperature;48%

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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