Forodesine

Base Information

• Chemical Name: Forodesine
• CAS No.: 209799-67-7
• Molecular Formula: C11H14N4O4
• Molecular Weight: 266.257
• Mol file: 209799-67-7.mol

Synonyms:4H-Pyrrolo[3,2-d]pyrimidin-4-one,7-[(2S,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-2-pyrrolidinyl]-1,5-dihydro-(9CI);Fodosine;Forodesine;Immucillin H;

Chemical Property of Forodesine

Chemical Property:

• Vapor Pressure: 6.61E-16mmHg at 25°C
• Refractive Index: 1.894
• Boiling Point: 613.5 °C at 760 mmHg
• PKA: 13.88±0.70(Predicted)
• Flash Point: 324.8 °C
• PSA: 134.26000
• Density: 2.01 g/cm³
• LogP: -1.69300
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere

Purity/Quality:

99%, ^*data from raw suppliers

Fodosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: Forodesine is a purine nucleoside analog and purine nucleoside phosphorylase (PNP) inhibitor (IC50s = 1.19, 0.48, 1.24, 0.66, and 1.57 nM for human, mouse, rat, monkey, and dog PNP, respectively). It inhibits phytohemagglutinin A-, mixed lymphocyte reaction-, or IL-2-induced proliferation of isolated human peripheral blood lymphocytes (PBLs; IC50s = <0.1-0.38 μM) in the presence, but not absence, of 2’-deoxyguanosine (dGuo). Forodesine inhibits proliferation of CEM-SS T cell acute lymphoblastic leukemia (T-ALL) cells. In vivo, forodesine (10 mg/kg) prolongs survival in the hu-PBL-SCID mouse model of xenogeneic graft versus host disease (GVHD).
• Uses: Treatment of T-Cell malignancies such as acute lymphoblastic leukemia (ALL) and cutaneous T-cell lymphoma (CTCL) Fodosine. Fodosine is a 23-pM inhibitor of bovine purine nucleoside phosphorylase (PNP) specifically designed as a transition state mimic.

Technology Process of Forodesine

There total 13 articles about Forodesine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(1S)-1-(7-N-benzyloxymethyl-9-deaza-6-O-methylhypoxanthin-9-yl)-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol (299916-67-9) → forodesine (209799-67-7)

Guidance literature:

With hydrogenchloride; In water; for 1h; Heating / reflux;

Reference yield:

(3aR,4R,6aS)-4-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)tetrahydro-2,2-dimethyl-3aH-[1,3]dioxolo[4,5-c]pyrrole (153172-31-7) → forodesine (209799-67-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: NCS / pentane / 1 h

1.2: LiTMP / tetrahydrofuran / -78 °C

2.1: 0.83 g / tetrahydrofuran / 1 h / -78 °C

3.1: 85 percent / CH₂Cl₂ / 16 h / 20 °C

4.1: dimethylformamide / 1 h / 65 - 70 °C

5.1: 0.68 g / aq. AcOH / tetrahydrofuran / 1.5 h / 20 °C

6.1: 3.46 g / NaOAc / methanol / 16 h / 20 °C

7.1: 3.68 g / DBU / CH₂Cl₂ / 4 h / Heating

8.1: 0.12 g / H₂ / Pd/C / ethanol / 3 h

9.1: 1.3 g / ethanol / 16 h / Heating

10.1: TFA / 20 °C

With N-chloro-succinimide; hydrogen; sodium acetate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; pentane; 1.1: Chlorination / 1.2: Elimination / 2.1: Addition / 3.1: Substitution / 4.1: Condensation / 5.1: Hydrolysis / 6.1: Condensation / 7.1: Substitution / 8.1: Hydrogenolysis / 9.1: Cyclization / 10.1: Hydrolysis;

DOI:10.1016/S0040-4020(00)00194-0

Reference yield:

(3aR,4R,6aS)-4-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-4,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole (153172-33-9) → forodesine (209799-67-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 0.83 g / tetrahydrofuran / 1 h / -78 °C

2: 85 percent / CH₂Cl₂ / 16 h / 20 °C

3: dimethylformamide / 1 h / 65 - 70 °C

4: 0.68 g / aq. AcOH / tetrahydrofuran / 1.5 h / 20 °C

5: 3.46 g / NaOAc / methanol / 16 h / 20 °C

6: 3.68 g / DBU / CH₂Cl₂ / 4 h / Heating

7: 0.12 g / H₂ / Pd/C / ethanol / 3 h

8: 1.3 g / ethanol / 16 h / Heating

9: TFA / 20 °C

With hydrogen; sodium acetate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 1: Addition / 2: Substitution / 3: Condensation / 4: Hydrolysis / 5: Condensation / 6: Substitution / 7: Hydrogenolysis / 8: Cyclization / 9: Hydrolysis;

DOI:10.1016/S0040-4020(00)00194-0

upstream raw materials:

(1S)-N-tert-butoxycarbonyl-5-O-tert-butyldimethylsilyl-1-(9-deazahypoxanthin-9-yl)-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol

(3aR,4R,6aS)-4-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)tetrahydro-2,2-dimethyl-3aH-[1,3]dioxolo[4,5-c]pyrrole

(3aR,4R,6aS)-4-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-4,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole

2-((3aS,4S,6R,6aR)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo [4,5-c]pyrrol-4-yl)acetonitrile

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