(2R,3R,5S,11S)-11-fluoro-8-methyl-3-[(trityloxy)methyl]-2,3-dihydro-9H-2,5-methanopyrimido[2,1-b][1,5,3]dioxazepin-9-one

Base Information

• Chemical Name: (2R,3R,5S,11S)-11-fluoro-8-methyl-3-[(trityloxy)methyl]-2,3-dihydro-9H-2,5-methanopyrimido[2,1-b][1,5,3]dioxazepin-9-one
• CAS No.: 128114-99-8
• Molecular Formula: C29H25 F N2 O4
• Molecular Weight: 484.527
• Mol file: 128114-99-8.mol

Synonyms:

Chemical Property of (2R,3R,5S,11S)-11-fluoro-8-methyl-3-[(trityloxy)methyl]-2,3-dihydro-9H-2,5-methanopyrimido[2,1-b][1,5,3]dioxazepin-9-one

Chemical Property:

• Vapor Pressure: 2.86E-14mmHg at 25°C
• Boiling Point: 598.2°Cat760mmHg
• Flash Point: 315.6°C
• Density: 1.31g/cm³

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2R,3R,5S,11S)-11-fluoro-8-methyl-3-[(trityloxy)methyl]-2,3-dihydro-9H-2,5-methanopyrimido[2,1-b][1,5,3]dioxazepin-9-one

There total 5 articles about (2R,3R,5S,11S)-11-fluoro-8-methyl-3-[(trityloxy)methyl]-2,3-dihydro-9H-2,5-methanopyrimido[2,1-b][1,5,3]dioxazepin-9-one 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%

1-(2-deoxy-2-fluoro-3-O-mesyl-5-O-triphenylmethyl-β-D-arabinofuranosyl)thymine (128114-98-7) → 2,3'-anhydro-1-(2-deoxy-2-fluoro-5-O-trityl-β-D-lyxofuranosyl)thymine (128114-99-8)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; for 8h; Heating;

DOI:10.1021/jm00109a017

Reference yield: 40.1%

1-(2-deoxy-2-fluoro-3-O-mesyl-5-O-triphenylmethyl-β-D-arabinofuranosyl)thymine (128114-98-7) → 2,3'-anhydro-1-(2-deoxy-2-fluoro-5-O-trityl-β-D-lyxofuranosyl)thymine (128114-99-8) + 1-(3-azido-2,3-dideoxy-2-fluoro-5-O-trityl-β-D-arabinofuranosyl)thymine

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; for 2h; Heating;

DOI:10.1021/jm00170a016

Reference yield:

trityl chloride (76-83-5) → 2,3'-anhydro-1-(2-deoxy-2-fluoro-5-O-trityl-β-D-lyxofuranosyl)thymine (128114-99-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) pyridine / 1.) 50 deg C, 2 h, 2.) 4 deg C, overnight

2: 85 percent / DBU / CH₂Cl₂ / 8 h / Heating

With pyridine; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane;

DOI:10.1021/jm00109a017

upstream raw materials:

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

trityl chloride

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

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

Downstream raw materials:

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

1-(3-deoxy-2,3-didehydro-2-fluoro-5-O-trityl-β-D-glycero-2-enopentofuranosyl)thymine