Cytidine, 2'-deoxy-2',2'-difluoro-N-(1-oxo-2-propylpentyl)-

Base Information

• Chemical Name: Cytidine, 2'-deoxy-2',2'-difluoro-N-(1-oxo-2-propylpentyl)-
• CAS No.: 892128-60-8
• Molecular Formula: C17H25F2N3O5
• Molecular Weight: 389.399
• UNII: YLR364XYSA
• ChEMBL ID: CHEMBL577711
• DSSTox Substance ID: DTXSID001025742
• Metabolomics Workbench ID: 153801
• NCI Thesaurus Code: C102856
• Nikkaji Number: J3.206.210E
• Wikidata: Q27294578
• Mol file: 892128-60-8.mol

Synonyms:LY2334737

Chemical Property of Cytidine, 2'-deoxy-2',2'-difluoro-N-(1-oxo-2-propylpentyl)-

Chemical Property:

• PKA: 9.66±0.20(Predicted)
• PSA: 117.17000
• Density: 1.41±0.1 g/cm3(Predicted)
• LogP: 1.11830
• Solubility.: Soluble in DMSO
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 389.17622723
• Heavy Atom Count: 27
• Complexity: 620

Purity/Quality:

98%min ^*data from raw suppliers

LY2334737 >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC(CCC)C(=O)NC1=NC(=O)N(C=C1)C2C(C(C(O2)CO)O)(F)F
• Isomeric SMILES: CCCC(CCC)C(=O)NC1=NC(=O)N(C=C1)[C@H]2C([C@@H]([C@H](O2)CO)O)(F)F
• Recent ClinicalTrials: A Study of LY2334737 in Participants With Cancer That is Advanced and/or Has Spread

Technology Process of Cytidine, 2'-deoxy-2',2'-difluoro-N-(1-oxo-2-propylpentyl)-

There total 9 articles about Cytidine, 2'-deoxy-2',2'-difluoro-N-(1-oxo-2-propylpentyl)- 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: 88.0%

C27H41F2N3O9 (1196664-00-2) → N-(1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)-2-propylpentanamide (892128-60-8)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 25 ℃; Inert atmosphere;

DOI:10.1021/jm901181h

Reference yield: 77.0%

C11H18N2O2 → N-(1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)-2-propylpentanamide (892128-60-8)

Guidance literature:

gemcitabine; With chloro-trimethyl-silane; In pyridine; at 0 ℃; for 2h;

C₁₁H₁₈N₂O₂; In pyridine; acetonitrile; at 0 - 45 ℃;

In pyridine; acetonitrile; at 0 - 45 ℃;

Reference yield: 77.0%

valproic acid (99-66-1) → N-(1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)-2-propylpentanamide (892128-60-8)

Guidance literature:

gemcitabine; With pyridine; chloro-trimethyl-silane; at 0 - 5 ℃; for 2h;

valproic acid; With 1,1'-carbonyldiimidazole; In acetonitrile; at 20 - 45 ℃;

With ethanol; phosphoric acid; water; more than 3 stages;

upstream raw materials:

valproic acid

C₂₇H₄₁F₂N₃O₉

gemcitabine hydrochloride

gemcitabine

Downstream raw materials:

1-(2,2-difluoro-2-deoxy-β-D-ribofuranosyl)-4-(2-propyl-1-oxopentyl)aminopyrimidin-2-one p-toluenesulfonic acid co-crystal

1-(2,2-difluoro-2-deoxy-β-D-ribofuranosyl)-4-(2-propyl-1-oxopentyl)aminopyrimidin-2-one benzensulfonic acid co-crystal

gemcitabine

Refernces

• 1、 -. "ORALLY ACTIVE PRODRUG OF GEMCITABINE". Page/Page column 23-24. . Retrieved 2020/06/10.
• 2、 -. "CRYSTALLINE FORMS OF GEMCITABINE AMIDE PRODRUG, COMPOSITIONS AND USE THEREOF". Page/Page column 6-7. . Retrieved 2008/06/13.