69-33-0

Basic information

• Product Name: TUBERCIDIN
• Synonyms: TUBERCIDIN;TUBERCIDINE;3-d)pyrimidin-4-amine,7-beta-d-ribofuranosyl-7h-pyrrolo(;3-d)pyrimidine,4-amino-7-beta-d-ribofuranosyl-7h-pyrrolo(;4-amino-7-(beta-d-ribofuranosyl)-pyrrolo(2,3-d)pyrimidine;4-amino-7-beta-d-ribofuranosyl-7h-pyrrolo(2,3-d)pyrimidine;7-beta-d-ribofuranosyl-7h-pyrrolo(2,3-d)pyrimidine-4-amine;7-deaza-adenosin
• CAS NO: 69-33-0
• Molecular Formula: C₁₁H₁₄N₄O₄
• Molecular Weight: 266.25
• EINECS: 200-703-4
• Mol File: 69-33-0.mol
• Article Data: 14

Chemical Properties

• Melting Point: 247-248 °C (decomp)(Solv: water (7732-18-5))
• Boiling Point: 409.46°C (rough estimate)
• Flash Point: 346.2 °C
• Appearance: off-white/
• Density: 1.2896 (rough estimate)
• Vapor Pressure: 1.02E-17mmHg at 25°C
• Refractive Index: 1.8340 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Soluble in DMSO
• PKA: 12.44±0.70(Predicted)
• Merck: 13,9875
• BRN: 38498
• CAS DataBase Reference: TUBERCIDIN(CAS DataBase Reference)
• NIST Chemistry Reference: TUBERCIDIN(69-33-0)
• EPA Substance Registry System: TUBERCIDIN(69-33-0)

Safety Data

• Hazard Codes: T+
• Statements: 28
• Safety Statements: 36/37/39-45
• RIDADR: UN 3462 6.1/PG 2
• WGK Germany: 3
• RTECS: UY8870000
• F: 10
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 69-33-0(Hazardous Substances Data)

Usage

Chemical Properties

White crystal

Uses

Tubercidin is a nucleoside metabolite first isolated from Streptomyces tubericidus. Tubercidin, like other nucleosides, is a broad spectrum, potent chemotherapeutic agent active against viruses, bacteria, fungi, protozoans and tumours. Tubercidin acts at a diverse range of sites, such as RNA processing, nucleic acid and protein synthesis, and acts as a nucleoside mimic of adenosine.

Definition

ChEBI: An N-glycosylpyrrolopyrimidine that is adenosine in which the in the 5-membered ring that is not attached to the ribose moiety is replaced by a carbon. Tubercidin is produced in the culture broth of Streptomyces tubericidus.

Biological Activity

tubercidin is an adenosine analog antibiotic agent.nucleoside antibiotics are a family of natural products with various biological functions. their biosynthesis is a complex process via multistep enzymatic reactions.

in vitro

previous study showed that tubercidin alone had a dose-dependent inhibitory effect on myeloid and erythroid human bone marrow progenitor cells. bfu-e were more sensitive at higher doses of tubercidin than cfu-gm. the 99% complete inhibition of bfu-e colonies was observed at 10 nm tubercidin, whereas complete inhibition of cfu-gm occurred at 100 nm [1].

in vivo

animal toxicity study showed that four successive daily injections of tubercidin at 5 mg/kg per day could produce 100% mouse mortality within 3 to 5 days, with massive peritonitis and intestinal obstruction. in addition, coadministration of nbmpr-p at 25 mg/kg per day could protect the mice from the tubercidin lethality and allow the repetition of the regimen for a second time with 100% survival [1].

IC 50

3.4 and 3.7 nm for granulocyte-macrophage cfu (cfu-gm) and erythroid burst-forming units (bfu-e), respectively

Purification Methods

7-Deazaadenosine forms needles from hot H2O. It is soluble in H2O (0.33%), MeOH (0.5%) and EtOH (0.05%). It has UV max at 270nm ( 12,100) in 0.001N NaOH. The picrate has m 229-231o(dec). [Tolman et al. J Am Chem Soc 91 2102 1969, Mizuno et al. J Org Chem 28 3329 1963, IR: Anzai et al. J Antibiot (Japan) [9] 10 201 1957, Beilstein 26 IV 1117.]

references

[1] el kouni mh,diop d,o'shea p,carlisle r,sommadossi jp. prevention of tubercidin host toxicity by nitrobenzylthioinosine 5'-monophosphate for the treatment of schistosomiasis. antimicrob agents chemother.1989 jun;33(6):824-7.[2] grage tb,rochlin db,weiss aj,wilson wl. clinical studies with tubercidin administered after absorption into human erythrocytes. cancer res.1970 jan;30(1):79-81.

InChI:InChI=1/C11H14N4O4/c12-9-5-1-2-15(10(5)14-4-13-9)11-8(18)7(17)6(3-16)19-11/h1-2,4,6-8,11,16-18H,3H2,(H2,12,13,14)/t6-,7-,8-,11-/m1/s1

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) → tubercidin (69-33-0)

Conditions	Yield
With ammonia In methanol at 130℃; for 16h;	85%

4-chloro-7-(β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidine (16754-80-6) → tubercidin (69-33-0)

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 (120401-34-5) → tubercidin (69-33-0)

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 (94773-30-5) → tubercidin (69-33-0)

Conditions	Yield
nickel In N,N-dimethyl acetamide for 4h; Heating;	67%

5-Bromotubercidin (21193-80-6) → tubercidin (69-33-0)

Conditions	Yield
With palladium on activated charcoal; ammonium formate In ethanol for 3h; Reflux;	65%

5-iodotubercidin (24386-93-4) → tubercidin (69-33-0)

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 (85335-76-8) → tubercidin (69-33-0) + 2'-O-methylthiomethyltubercidin (90813-69-7) + 4-amino-7-(β-D-arabinofuranosyl)pyrrolo<2,3-d>pyrimidine (64526-34-7)

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 (102690-94-8) → tubercidin (69-33-0)

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 (115479-39-5) → tubercidin (69-33-0)

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 (75921-20-9) → tubercidin (69-33-0)

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 (120401-29-8) → tubercidin (69-33-0)

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 (16754-86-2) → tubercidin (69-33-0)

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

4-chloro-1H-pyrrolo[2,3-d]pyrimidine (3680-69-1) → tubercidin (69-33-0)

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 (85572-94-7) → tubercidin (69-33-0)

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

2,3-O-isopropylidene-5-O-(tertbutyldimethyl)-α-D-ribofuranosyl chloride → tubercidin (69-33-0)

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

4-chloro-1H-pyrrolo[2,3-d]pyrimidine → tubercidin (69-33-0)

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

4-chloro-2,3-O-isopropylidene-5-O-(tertbutyldimethylsilyl)-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine → tubercidin (69-33-0)

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 (69-33-0) → 4-amino-7-(2,3-anhydro-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine (40627-31-4)

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 (69-33-0) → (2R,3R,4S,5R)-2-(4-Amino-3-oxy-pyrrolo[2,3-d]pyrimidin-7-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In methanol Ambient temperature;	97%

tubercidin (69-33-0) → 7-β-D-ribofuranosylpyrrolo<2,3-d>pyrimidin-4-one (2862-16-0)

Conditions	Yield
With acetic acid; sodium nitrite at 60℃; for 12h;	96%

N,N'-bis(dimethylaminomethylene)hydrazine (16114-05-9) + tubercidin (69-33-0) → 7-(β-D-ribofuranosyl)-4-(1,2,4-triazol-4-yl)pyrrolo<2,3-d>pyrimidine (163632-56-2)

Conditions	Yield
With pyridine at 100℃; for 24h;	95%

2-chloroethanal (107-20-0) + tubercidin (69-33-0) → N1-deazaethenoadenosine (53437-77-7)

Conditions	Yield
In DMF (N,N-dimethyl-formamide) at 50℃; for 20h;	94%

tubercidin (69-33-0) + acetic anhydride (108-24-7) → 4-acetylamino-7-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

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%

tubercidin (69-33-0) + acetic anhydride (108-24-7) → 2',3',5'-tri-O-acetyltubercidin (60343-84-2)

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 (69-33-0) + 2,2-dimethoxy-propane (77-76-9) → ((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)

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 (69-33-0) + N,N-dimethylformamide diethyl diacetal (1188-33-6) → 4-<<(dimethylamino)methylidene>amino>-7-(β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidine (57881-19-3)

Conditions	Yield
In N,N-dimethyl-formamide at 50℃; for 1h;	85%

tubercidin (69-33-0) → (2R,3R,4S,5S)-2-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(chloromethyl)tetrahydrofuran-3,4-diol (53458-85-8)

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 (69-33-0) + tert-butyldimethylsilyl chloride (18162-48-6) → 2',3',5'-Tri-O-(tert-butyldimethylsilyl)tubercidin (87119-54-8)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide for 18h; Ambient temperature;	71%

di(rhodium)tetracarbonyl dichloride + tubercidin (69-33-0) → dicarbonylchloro(7-desazaadenosin)rhodium(I)

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%

tubercidin (69-33-0) + p-toluenesulfonyl chloride (98-59-9) → 2'-O-tosyltubercidin

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 (69-33-0) + (S)-2-tert-Butoxycarbonylamino-4-((S)-3-tert-butoxycarbonylamino-3-ethoxycarbonyl-propyldisulfanyl)-butyric acid ethyl ester (144385-04-6) → (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	Yield
With pyridine; triethylphosphine for 120h; Ambient temperature;	66%

tubercidin (69-33-0) + (2S,2'S)-dimethyl 4,4'-disulfanediylbis(2-(2,2,2-trifluoroacetamido)butanoate) (84355-09-9) → (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)

Conditions	Yield
With tributylphosphine In pyridine for 96h; Ambient temperature;	62%

tubercidin (69-33-0) → 5-[131I]iodotubercidin

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 (69-33-0) + trityl chloride (76-83-5) → N6,5'-O-ditrityltubercidin (112135-89-4) + 5'-O-trityltubercidin (40983-03-7)

Conditions	Yield
With pyridine for 48h; Ambient temperature;	A 22% B 57%

tubercidin (69-33-0) + (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

Conditions	Yield
With pyridine; triethylphosphine for 96h; Ambient temperature;	55%

tubercidin (69-33-0) + prenyl bromide (870-63-3) → N4-(Δ2-Isopentenyl)tubercidin (23589-13-1)

Conditions	Yield
In N,N,N,N,N,N-hexamethylphosphoric triamide for 24h; Heating;	54%

tubercidin (69-33-0) + (S)-4-[(S)-3-Ethoxycarbonyl-3-(2-methoxy-acetylamino)-propyldisulfanyl]-2-(2-methoxy-acetylamino)-butyric acid ethyl ester (144373-81-9) → N-(methoxyacetyl)-S-tubercidinyl-L-homocysteine ethyl ester

Conditions	Yield
With pyridine; triethylphosphine for 60h; Ambient temperature;	54%

tubercidin (69-33-0) + (S)-2-(2-Methoxy-acetylamino)-4-[(S)-3-(2-methoxy-acetylamino)-3-propoxycarbonyl-propyldisulfanyl]-butyric acid propyl ester (144373-82-0) → N-(methoxyacetyl)-S-tubercidinyl-L-homocysteine propyl ester

Conditions	Yield
With pyridine; triethylphosphine for 96h; Ambient temperature;	54%

tubercidin (69-33-0) + (S)-4-[(S)-3-Isopropoxycarbonyl-3-(2-methoxy-acetylamino)-propyldisulfanyl]-2-(2-methoxy-acetylamino)-butyric acid isopropyl ester (144373-83-1) → (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	Yield
With pyridine; triethylphosphine for 96h; Ambient temperature;	53%

tubercidin (69-33-0) + (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-[(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	Yield
With pyridine; triethylphosphine for 70h; Ambient temperature;	53%

tubercidin (69-33-0) + (S)-2-Acetylamino-4-((S)-3-acetylamino-3-propoxycarbonyl-propyldisulfanyl)-butyric acid propyl ester (144373-79-5) → N-acetyl-S-tubercidinyl-L-homocysteine propyl ester

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

Upstream product

• 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 
• 94773-30-5 4-Amino-2-(methylthio)-7-(β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin 
• 16754-80-6 4-chloro-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 
• 102690-94-8 2,3-O-isopropylidene-5-O-(tert-butyldimethylsilyl)-α-D-ribofuranosyl chloride 
• 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 
• 75921-20-9 5-O-<(1,1-dimethylethyl)dimethylsilyl>-2,3-O-(1-methylethylidene)-β-D-ribofuranose 
• 21193-61-3 4-amino-5-bromo-7-(β-L-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 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 
• 21193-80-6 5-Bromotubercidin 
• 24386-93-4 5-iodotubercidin 
• 85572-94-7 4-chloro-2-(methylthio)-7-(β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidine 
• 3680-69-1 4-chloro-1H-pyrrolo[2,3-d]pyrimidine 
• 16754-86-2 4-(methylthio)-7-(β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidine 

Downstream Products

• 78000-56-3 7-deaza-8-bromoadenosine 
• 40725-89-1 4-amino-N7-(3'-deoxy-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine 
• 1338466-77-5 1-(3-((((2R,3S,4R,5R)-5-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl) (isopropyl)amino)propyl)-3-(4-(tertbutyl)phenyl)urea 
• 52017-19-3 4-furfurylamino-7-β-D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidine 
• 16719-46-3 tubercidin 5'-monophosphate 
• 18555-63-0 N-(7-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)benzamide 
• 57913-63-0 N-(phenylmethyl)-7-β-D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine 

Relevant articles and documents

SYNTHESIS AND STRUCTURE OF HIGH POTENCY RNA THERAPEUTICS

This invention provides expressible polynucleotides, which can express a target protein or polypeptide. Synthetic mRNA constructs for producing a protein or polypeptide can contain one or more 5′ UTRs, where a 5′ UTR may be expressed by a gene of a plant. In some embodiments, a 5′ UTR may be expressed by a gene of a member of Arabidopsis genus. The synthetic mRNA constructs can be used as pharmaceutical agents for expressing a target protein or polypeptide in vivo.

ADENOSINE ANALOG AND ITS USE IN REGULATING THE CIRCADIAN CLOCK

Provided are a kind of nucleoside analogue compounds, and compositions comprising these compounds and pentostatin, their use for modulating circadian rhythm, preferably, for shifting circadian phase, and methods for modulating circadian rhythm, preferably, for shifting circadian phase via these compounds or the compositions.

Glycosylation of Pyrrolo[2,3- d]pyrimidines with 1- O-Acetyl-2,3,5-tri- O-benzoyl-β- d -ribofuranose: Substituents and Protecting Groups Effecting the Synthesis of 7-Deazapurine Ribonucleosides

Glycosylation of nonfunctionalized 6-chloro-7-deazapurine with commercially available 1-O-acetyl-2,3,5-tri-O-benzoyl-β-d-ribofuranose (45%) followed by amination and deprotection gave tubercidin in only two steps. Similar conditions applied for the synthe