5-Fluoro-1-[4-hydroxy-5-(trityloxymethyl)oxolan-2-yl]pyrimidine-2,4-dione

Base Information

• Chemical Name: 5-Fluoro-1-[4-hydroxy-5-(trityloxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS No.: 10343-71-2
• Molecular Formula: C₂₈H₂₅FN₂O₅
• Molecular Weight: 488.515
• NSC Number: 125563
• DSSTox Substance ID: DTXSID60298709
• Mol file: 10343-71-2.mol

Synonyms:10343-71-2;1-(2-deoxy-5-o-tritylpentofuranosyl)-5-fluoropyrimidine-2,4(1h,3h)-dione;5-fluoro-1-[4-hydroxy-5-(trityloxymethyl)oxolan-2-yl]pyrimidine-2,4-dione;5-Fluoro-1-(4-hydroxy-5-((trityloxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione;NSC125563;DTXSID60298709;NSC-125563

Chemical Property of 5-Fluoro-1-[4-hydroxy-5-(trityloxymethyl)oxolan-2-yl]pyrimidine-2,4-dione

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 93.55000
• Density: 1.38g/cm³
• LogP: 3.33280
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 488.17475006
• Heavy Atom Count: 36
• Complexity: 771

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=C(C(=O)NC2=O)F)COC(C3=CC=CC=C3)(C4=CC=CC=C4)C5=CC=CC=C5)O

Technology Process of 5-Fluoro-1-[4-hydroxy-5-(trityloxymethyl)oxolan-2-yl]pyrimidine-2,4-dione

There total 2 articles about 5-Fluoro-1-[4-hydroxy-5-(trityloxymethyl)oxolan-2-yl]pyrimidine-2,4-dione 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: 84.4%

trityl chloride (76-83-5) + 5-Fluoro-2'-deoxyuridine (50-91-9) → 1-(2-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)-5-fluorouracil (4031-24-7,10343-71-2,103285-11-6)

Guidance literature:

With pyridine; for 1h; Heating;

DOI:10.1002/jps.2600740305

Reference yield: 69.0%

→ 1-(2-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)-5-fluorouracil (4031-24-7,10343-71-2,103285-11-6)

Guidance literature:

Reference yield: 86.0%

methanesulfonyl chloride (124-63-0) + 1-(2-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)-5-fluorouracil (4031-24-7,10343-71-2,103285-11-6) → 1-(2-deoxy-3-O-mesyl-5-O-trityl-β-D-threo-pentofuranosyl)-5-fluorouracil (1456615-51-2)

Guidance literature:

With pyridine; at 20 ℃; for 2h;

DOI:10.1016/j.ejmech.2013.06.047

upstream raw materials:

trityl chloride

5-Fluoro-2'-deoxyuridine

Downstream raw materials:

2,3'-anhydro-1-(2-deoxy-5-O-trityl-β-D-threo-pentofuranosyl)-5-fluorouracil

1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-trityloxymethyl-tetrahydro-furan-2-yl]-5-fluoro-1H-pyrimidine-2,4-dione

2'-deoxy-3'-O-benzyl-5'-O-trityl-5-fluorouridine

1-[(2R,4S,5R)-4-(4-tert-Butyl-benzyloxy)-5-trityloxymethyl-tetrahydro-furan-2-yl]-5-fluoro-1H-pyrimidine-2,4-dione