1-(3-deoxy-2-fluoro-5-O-trityl-β-D-arabinofuranosyl)thymine

Base Information

• Chemical Name: 1-(3-deoxy-2-fluoro-5-O-trityl-β-D-arabinofuranosyl)thymine
• CAS No.: 128114-97-6
• Molecular Formula: C₂₉H₂₇FN₂O₅
• Molecular Weight: 502.542
• Mol file: 128114-97-6.mol

Synonyms:1-(3-deoxy-2-fluoro-5-O-trityl-β-D-arabinofuranosyl)thymine

Chemical Property of 1-(3-deoxy-2-fluoro-5-O-trityl-β-D-arabinofuranosyl)thymine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(3-deoxy-2-fluoro-5-O-trityl-β-D-arabinofuranosyl)thymine

There total 4 articles about 1-(3-deoxy-2-fluoro-5-O-trityl-β-D-arabinofuranosyl)thymine 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: 85.0%

trityl chloride (76-83-5) + 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)thymine (69256-17-3,163252-36-6,2923-73-1) → 1-(2-deoxy-2-fluoro-5-O-trityl-β-D-arabinofuranosyl)thymine (128114-97-6)

Guidance literature:

With pyridine; 1.) RT, 2.) 100 deg C, 90 min;

DOI:10.1021/jm00170a016

Reference yield: 20.0%

1-(2,3-epoxy-5-O-trityl-β-D-lyxo-pentofuranosyl)thymine (115913-84-3) → 1-(3-deoxy-2-fluoro-5-O-trityl-β-D-arabinofuranosyl)thymine (128114-97-6) + 1-(3-deoxy-3-fluoro-5-O-trityl-β-D-arabinofuranosyl)thymine

Guidance literature:

With potassium hydrogen bifluoride; sodium fluoride; In 2-ethoxy-ethanol; for 26h; regioselective reaction; Reflux;

DOI:10.1021/jm100803c

Reference yield:

5-methyl-5'-O-(triphenylmethyl)uridine 2',3'-bis(methanesulfonate) (124493-84-1) → 1-(3-deoxy-2-fluoro-5-O-trityl-β-D-arabinofuranosyl)thymine (128114-97-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / 1 N NaOH / ethanol / 3 h / 60 °C

2: KHF₂ / 2-ethoxy-ethanol / 15 h / 145 °C

With sodium hydroxide; potassium hydrogen bifluoride; In 2-ethoxy-ethanol; ethanol;

DOI:10.1021/jm00109a017

upstream raw materials:

trityl chloride

1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)thymine

1-(2,3-epoxy-5-O-trityl-β-D-lyxo-pentofuranosyl)thymine

5-methyl-5'-O-(triphenylmethyl)uridine 2',3'-bis(methanesulfonate)

Downstream raw materials:

1-(2-deoxy-2-fluoro-β-D-xylofuranosyl)thymine

1-(3-azido-2,3-dideoxy-2-fluoro-β-D-arabinofuranosyl)thymine

2,3'-anhydro-1-(2-deoxy-2-fluoro-5-O-trityl-β-D-lyxofuranosyl)thymine

1-(2-deoxy-2-fluoro-3-O-mesyl-5-O-triphenylmethyl-β-D-arabinofuranosyl)thymine