((2R,3R,4R,5R)-3-(benzoyloxy)-5-chloro-4-fluoro-4-methyltetrahydrofuran-2-yl)methyl benzoate

Base Information

• Chemical Name: ((2R,3R,4R,5R)-3-(benzoyloxy)-5-chloro-4-fluoro-4-methyltetrahydrofuran-2-yl)methyl benzoate
• CAS No.: 1199809-23-8
• Molecular Formula: C20H18ClFO5
• Molecular Weight: 392.811
• Mol file: 1199809-23-8.mol

Synonyms:((2R,3R,4R,5R)-3-(benzoyloxy)-5-chloro-4-fluoro-4-methyltetrahydrofuran-2-yl)methyl benzoate

Chemical Property of ((2R,3R,4R,5R)-3-(benzoyloxy)-5-chloro-4-fluoro-4-methyltetrahydrofuran-2-yl)methyl benzoate

Chemical Property:

• PSA: 61.83000
• LogP: 3.76090

Purity/Quality:

95%-98% ^*data from raw suppliers

(2R)-2-Deoxy-2-fluoro-2-methyl-α-D-erythro-pentofuranosylChloride3,5-Dibenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (2R)-2-Deoxy-2-fluoro-2-methyl-α-D-erythro-pentofuranosyl Chloride?3,5-Dibenzoate?has utility in the stereoselective synthesis of β-D-2''-Deoxy-2''-α-fluoro-2''-β-C-methyl-3'',5''-cyclic phosphate nucleotide, a prodrug for treating hepatitis C virus (HCV) infection. It is also a related compound of (2R)-2-Deoxy-2-fluoro-2-methyl-β-D-erythro-pentofuranose?3,5-Dibenzoate (D235550) and (2R)-2-Deoxy-2-fluoro-2-methyl-α-D-erythro-pentofuranose 3,5-Dibenzoate (D235555).

Technology Process of ((2R,3R,4R,5R)-3-(benzoyloxy)-5-chloro-4-fluoro-4-methyltetrahydrofuran-2-yl)methyl benzoate

There total 9 articles about ((2R,3R,4R,5R)-3-(benzoyloxy)-5-chloro-4-fluoro-4-methyltetrahydrofuran-2-yl)methyl benzoate 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: 95.0%

((2R,3R,4R,5R)-3-(benzoyloxy)-4-fluoro-5-hydroxy-4-methyltetrahydrofuran-2-yl)methyl benzoate (1199809-22-7) → ((2R,3R,4R,5R)-3-(benzoyloxy)-5-chloro-4-fluoro-4-methyltetrahydrofuran-2-yl)methyl benzoate (1199809-23-8,1500076-79-8)

Guidance literature:

With N-chloro-succinimide; triphenylphosphine; In dichloromethane; at 0 - 20 ℃; for 1h;

Reference yield:

C21H21FO6 → ((2R,3R,4R,5R)-3-(benzoyloxy)-5-chloro-4-fluoro-4-methyltetrahydrofuran-2-yl)methyl benzoate (1199809-23-8,1500076-79-8)

Guidance literature:

With thionyl chloride; In methanol; at 0 - 30 ℃; Inert atmosphere;

Reference yield:

((2R,3R,4R,5R)-3-(benzoyloxy)-4-fluoro-5-hydroxy-4-methyltetrahydrofuran-2-yl)methyl benzoate (1199809-22-7) → ((2R,3R,4R,5S)-3-(benzoyloxy)-5-chloro-4-fluoro-4-methyltetrahydrofuran-2-yl)methyl benzoate (1500076-79-8) + ((2R,3R,4R,5R)-3-(benzoyloxy)-5-chloro-4-fluoro-4-methyltetrahydrofuran-2-yl)methyl benzoate (1199809-23-8,1500076-79-8)

Guidance literature:

With N-chloro-succinimide; triphenylphosphine; In dichloromethane; at 0 - 20 ℃; for 1h; optical yield given as %de;

DOI:10.1021/jo200060f

upstream raw materials:

((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate

((2R,3R,4R,5R)-3-(benzoyloxy)-4-fluoro-5-hydroxy-4-methyltetrahydrofuran-2-yl)methyl benzoate

3,5-di-O-benzoyl-2-C-methyl-D-ribono-γ-lactone

3.5-Di-O-benzoyl-2-C-methyl-α-D-ribofuranose

Downstream raw materials:

(2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate