((2R,3S)-3-(4-fluorophenyl)-5-oxotetrahydrofuran-2-yl)methyl methanesulfonate

Base Information

Chemical Name:((2R,3S)-3-(4-fluorophenyl)-5-oxotetrahydrofuran-2-yl)methyl methanesulfonate
CAS No.:1423027-17-1
Molecular Formula:C₁₂H₁₃FO₅S
Molecular Weight:288.297
Hs Code.:

Synonyms:((2R,3S)-3-(4-fluorophenyl)-5-oxotetrahydrofuran-2-yl)methyl methanesulfonate

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Chemical Property of ((2R,3S)-3-(4-fluorophenyl)-5-oxotetrahydrofuran-2-yl)methyl methanesulfonate

Chemical Property:

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Technology Process of ((2R,3S)-3-(4-fluorophenyl)-5-oxotetrahydrofuran-2-yl)methyl methanesulfonate

There total 5 articles about ((2R,3S)-3-(4-fluorophenyl)-5-oxotetrahydrofuran-2-yl)methyl methanesulfonate 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: 92.0%

: 950838-19-4
(4S,5R)-4-(4-fluorophenyl)-5-(hydroxymethyl)dihydrofuran-2(3H)-one

: 124-63-0
methanesulfonyl chloride

: 1423027-17-1
((2R,3S)-3-(4-fluorophenyl)-5-oxotetrahydrofuran-2-yl)methyl methanesulfonate

Guidance literature:: With triethylamine; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;
DOI:10.1039/c3ob27321k

Reference yield:

: 1423027-07-9,918149-75-4
3-(4-fluorophenyl)pent-4-enoic acid

: 1423027-17-1
((2R,3S)-3-(4-fluorophenyl)-5-oxotetrahydrofuran-2-yl)methyl methanesulfonate

Guidance literature:: Multi-step reaction with 4 steps

1: iodine / acetonitrile / 24 h / 0 °C / Inert atmosphere; Darkness

2: sodium carbonate / methanol / Inert atmosphere; Reflux

3: (acetao)(aqua)(S,S)-N,N′-bis(3,5-di-tert-butylsalicylidene-1,2-cyclohexanediamino)-cobalt(III); water / 12 h / 0 - 25 °C / Resolution of racemate

4: triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

With (acetao)(aqua)(S,S)-N,N′-bis(3,5-di-tert-butylsalicylidene-1,2-cyclohexanediamino)-cobalt(III); water; iodine; sodium carbonate; triethylamine; In methanol; dichloromethane; acetonitrile;
DOI:10.1039/c3ob27321k

Reference yield:

: 124980-95-6,7361-55-9
3-(4-fluorophenyl)prop-2-en-1-ol

: 1423027-17-1
((2R,3S)-3-(4-fluorophenyl)-5-oxotetrahydrofuran-2-yl)methyl methanesulfonate

Guidance literature:: Multi-step reaction with 5 steps

1: hexanoic acid / ethanol / 70 - 150 °C / Reflux

2: iodine / acetonitrile / 24 h / 0 °C / Inert atmosphere; Darkness

3: sodium carbonate / methanol / Inert atmosphere; Reflux

4: (acetao)(aqua)(S,S)-N,N′-bis(3,5-di-tert-butylsalicylidene-1,2-cyclohexanediamino)-cobalt(III); water / 12 h / 0 - 25 °C / Resolution of racemate

5: triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

With (acetao)(aqua)(S,S)-N,N′-bis(3,5-di-tert-butylsalicylidene-1,2-cyclohexanediamino)-cobalt(III); water; iodine; sodium carbonate; triethylamine; hexanoic acid; In methanol; ethanol; dichloromethane; acetonitrile; 1: |Johnson-Claisen Rearrangement;
DOI:10.1039/c3ob27321k