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

Base Information

• Chemical Name: ((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methyl benzoate
• CAS No.: 874638-80-9
• Molecular Formula: C20H17FO6
• Molecular Weight: 372.35
• Mol file: 874638-80-9.mol

Synonyms:[(2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxooxolan-2-yl]methyl benzoate;;

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

Chemical Property:

• Melting Point: 133 oC
• Boiling Point: 458.6±34.0 °C(Predicted)
• PSA: 78.90000
• Density: 1.33
• LogP: 2.72260
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

3,5-Di-O-benzoyl-2-deoxy-2-fluoro-2C-methyl-D-ribono-1,4-lactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: neuromuscular blocking agent (2R)-2-Deoxy-2-fluoro-2-methyl-D-erythropentonic Acid γ-Lactone 3,5-Dibenzoate is a reactant used in the synthesis of 1''-C-cyano-2''-fluoro-2''-C-methyl pyrimidine nucleosides as HCV polymerase inhibitors.

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

There total 44 articles about ((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-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,4S)-4-fluoro-2,5-dihydroxy-4-methylpentane-1,3-diyl] dibenzoate → ((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate (874638-80-9,1033394-94-3)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 12h; Reagent/catalyst; Solvent; Temperature; Molecular sieve;

Reference yield: 95.0%

C11H19FO5 (1033394-83-0) + benzoyl chloride (98-88-4) → ((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate (874638-80-9,1033394-94-3)

Guidance literature:

C₁₁H₁₉FO₅; With hydrogenchloride; In ethanol; water; at 20 ℃; for 22h;

benzoyl chloride; With pyridine; In water; acetonitrile; at 0 - 30 ℃; for 1.16667h; Temperature;

Reference yield: 91.0%

(3R,4R,5R)-3-methyl-3-fluoro-4-benzoyloxy-5-hydroxymethylbutyrolactone + benzoyl chloride (98-88-4) → ((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate (874638-80-9,1033394-94-3)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃;

upstream raw materials:

(3R,4R,5R)-3?fluoro?4?hydroxy?5?(hydroxymethyl)?3?methyltetrahydrofuran?2?one

benzoyl chloride

(2S,3R)-3-[(4R)-2,2-dimethyl-[1,3]dioxolane-4-yl]-2,3-dihydroxy-2-methylpropionic acid ethyl ester

C₁₀H₁₈O₆

Downstream raw materials:

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

C₂₇H₂₂FN₅O₅

C₂₉H₂₇FN₄O₇S₂

(2R,3R,4R,5S)-5-(2-amino-6-chloro-9H-purin-9-yl)-2-(benzoyloxymethyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate

Refernces

• 1、 -. "Preparation method of anti-hepatitis C medicine sofosbuvir". Paragraph 0052; 0061-0062. . Retrieved 2020/07/02.
• 2、 -. "Method for preparing sofosbuvir intermediate". . . Retrieved 2019/04/17.