5'-Deoxy-5-fluoro-N4-(3-methyl-1-butyloxycarbonyl)cytidine

Base Information

• Chemical Name: 5'-Deoxy-5-fluoro-N4-(3-methyl-1-butyloxycarbonyl)cytidine
• CAS No.: 162204-30-0
• Molecular Formula: C15H22 F N3 O6
• Molecular Weight: 359.355
• Hs Code.: 29339900
• European Community (EC) Number: 813-824-8
• UNII: T83E758HO7
• DSSTox Substance ID: DTXSID50167334
• Wikidata: Q27289796
• ChEMBL ID: CHEMBL2041684
• Mol file: 162204-30-0.mol

Synonyms:162204-30-0;Isopentyl (1-((2R,3R,4S,5R)-3,4-dihydroxy-5-methyltetrahydrofuran-2-yl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl)carbamate;Capecitabine impurity F;5'-Deoxy-5-fluoro-N4-(3-methyl-1-butyloxycarbonyl)cytidine;5'-Deoxy-5-fluoro-N-[(3-methylbutoxy)carbonyl]cytidine;UNII-T83E758HO7;T83E758HO7;5'-Deoxy-5-fluoro-N4-(isopentyloxycarbonyl)cytidine;3-methylbutyl N-[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxopyrimidin-4-yl]carbamate;Cytidine, 5'-deoxy-5-fluoro-N-[(3-methylbutoxy)carbonyl]-;3-methylbutyl N-{1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl}carbamate;CYTIDINE, 5'-DEOXY-5-FLUORO-N-((3-METHYLBUTOXY)CARBONYL)-;SCHEMBL284973;CHEMBL2041684;DTXSID50167334;AKOS016008206;AS-80468;CS-0145351;F19397;A899353;Q27289796;5/'-Deoxy-5-fluoro-N4-(3-methyl-1-butyloxycarbonyl)cytidine;(5'-DEOXY-5-FLUORO-N4-(3-METHYL-1-BUTYLOXYCARBONYL)CYTIDINE);5'-Deoxy-5-fluoro-N4-(isopentyloxycarbonyl)cytidine (Capecitabine impurity);3-Methylbutyl [1-(5-Deoxy-beta-D-ribofuranosyl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl]carbamate;5'-deoxy-5-fluoro-n4-(isopentyloxycarbonyl)cytidine;5'-deoxy-5-fluoro-n-((3-methylbutoxy)carbonyl)cytidine;CARBAMIC ACID, (1-(5-DEOXY-.BETA.-D-RIBOFURANOSYL)-5-FLUORO-1,2-DIHYDRO-2-OXO-4-PYRIMIDINYL)-, 3-METHYLBUTYL ESTER;Isopentyl(1-((2R,3R,4S,5R)-3,4-dihydroxy-5-methyltetrahydrofuran-2-yl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl)carbamate

Chemical Property of 5'-Deoxy-5-fluoro-N4-(3-methyl-1-butyloxycarbonyl)cytidine

Chemical Property:

• Melting Point: 106-109°C
• PKA: 5.44±0.40(Predicted)
• PSA: 126.40000
• Density: 1.49±0.1 g/cm3(Predicted)
• LogP: 0.62970
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Methanol (Slightly)
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 359.14926359
• Heavy Atom Count: 25
• Complexity: 594

Purity/Quality:

97% ^*data from raw suppliers

5''-Deoxy-5-fluoro-N-[(3-methylbutoxy)carbonyl]cytidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(O1)N2C=C(C(=NC2=O)NC(=O)OCCC(C)C)F)O)O
• Isomeric SMILES: C[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=C(C(=NC2=O)NC(=O)OCCC(C)C)F)O)O
• Uses: 5''-Deoxy-5-fluoro-N-[(3-methylbutoxy)carbonyl]cytidine (Capecitabine EP Impurity E) is a 5''-Desoxycytidine derivative and is used as an antitumor agent. 5'-Deoxy-5-fluoro-N-[(3-methylbutoxy)carbonyl]cytidine is 5' Desoxycytidine derivatives are used as antitumor agents.

Technology Process of 5'-Deoxy-5-fluoro-N4-(3-methyl-1-butyloxycarbonyl)cytidine

There total 1 articles about 5'-Deoxy-5-fluoro-N4-(3-methyl-1-butyloxycarbonyl)cytidine 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:

carbonochloridic acid 3-methyl-butyl ester (628-50-2) → 5'-deoxy-5-fluoro-N4-(3-methyl-1-butyloxycarbonyl)cytidine (162204-30-0)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / acetone / 20 - 30 °C / Inert atmosphere

2: sodium hydroxide / acetone / 2 h / -15 - 10 °C

With potassium carbonate; sodium hydroxide; In acetone;

DOI:10.1016/j.ejmech.2012.06.023

upstream raw materials:

carbonochloridic acid 3-methyl-butyl ester