(R)-(-)-3-cyclohexyl-3-(4-fluorophenyl)-3-hydroxypropyl toluenesulfonate

Base Information

Chemical Name:(R)-(-)-3-cyclohexyl-3-(4-fluorophenyl)-3-hydroxypropyl toluenesulfonate
CAS No.:154808-45-4
Molecular Formula:C₂₂H₂₇FO₄S
Molecular Weight:406.518
Hs Code.:

Synonyms:

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Chemical Property of (R)-(-)-3-cyclohexyl-3-(4-fluorophenyl)-3-hydroxypropyl toluenesulfonate

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Technology Process of (R)-(-)-3-cyclohexyl-3-(4-fluorophenyl)-3-hydroxypropyl toluenesulfonate

There total 11 articles about (R)-(-)-3-cyclohexyl-3-(4-fluorophenyl)-3-hydroxypropyl toluenesulfonate 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: 45.0%

: 98-59-9
p-toluenesulfonyl chloride

: (R)-1-Cyclohexyl-1-(4-fluoro-phenyl)-propane-1,3-diol

: 154808-45-4
(R)-(-)-3-cyclohexyl-3-(4-fluorophenyl)-3-hydroxypropyl toluenesulfonate

Guidance literature:: With dmap; triethylamine; In dichloromethane; for 4h; Ambient temperature;
DOI:10.3891/acta.chem.scand.47-1019

Reference yield:

: 133216-88-3,112497-25-3
(+/-)-1-cyclohexyl-3-(trimethylsilyl)-2-propynol

: 154808-45-4
(R)-(-)-3-cyclohexyl-3-(4-fluorophenyl)-3-hydroxypropyl toluenesulfonate

Guidance literature:: Multi-step reaction with 9 steps

1: 86 percent / Red-Al (sodium bis(2-methoxyethoxy)aluminium hydride / toluene; diethyl ether / 16 h / Heating

2: Ti(OiPr)4, (+)-diisopropyl L-tartrate, 4 A molecular sieves, tert-butyl hydroperoxide / CH₂Cl₂ / 17.5 h / -23 °C

3: 1.) oxalyl chloride, DMSO, 2.) triethylamine / 1.) CH₂Cl₂, -70 deg C, 20 min, 2.) CH₂Cl₂, from -70 to -15 deg C

4: 83 percent / diethyl ether / -70 - 0 °C

5: 1.) Ti(OiPr)4, 2.) LiBH₄ / 1.) toluene, RT, 45 min, 2.) toluene, RT, 1 h

6: 63 percent / pyridine / tetrahydrofuran; toluene

7: 100 percent / TBAF (tetrabutylammonium fluoride) / tetrahydrofuran / 3 h

8: 1.) 9-borabicyclo<3.3.1>nonane, 2.) aq. NaOH, aq. H₂O₂ / 1.) THF, reflux, 10 h, 2.) THF, 50 deg C, 2 h

9: 45 percent / 4-(dimethylamino)pyridine, Et₃N / CH₂Cl₂ / 4 h / Ambient temperature

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium hydroxide; lithium borohydride; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; L-(+)-diisopropyl tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; dihydrogen peroxide; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.3891/acta.chem.scand.47-1019

Reference yield:

: 112497-26-4
(E)-(+/-)-1-cyclohexyl-3-(trimethylsilyl)-2-propenol

: 154808-45-4
(R)-(-)-3-cyclohexyl-3-(4-fluorophenyl)-3-hydroxypropyl toluenesulfonate

Guidance literature:: Multi-step reaction with 8 steps

1: Ti(OiPr)4, (+)-diisopropyl L-tartrate, 4 A molecular sieves, tert-butyl hydroperoxide / CH₂Cl₂ / 17.5 h / -23 °C

2: 1.) oxalyl chloride, DMSO, 2.) triethylamine / 1.) CH₂Cl₂, -70 deg C, 20 min, 2.) CH₂Cl₂, from -70 to -15 deg C

3: 83 percent / diethyl ether / -70 - 0 °C

4: 1.) Ti(OiPr)4, 2.) LiBH₄ / 1.) toluene, RT, 45 min, 2.) toluene, RT, 1 h

5: 63 percent / pyridine / tetrahydrofuran; toluene

6: 100 percent / TBAF (tetrabutylammonium fluoride) / tetrahydrofuran / 3 h

7: 1.) 9-borabicyclo<3.3.1>nonane, 2.) aq. NaOH, aq. H₂O₂ / 1.) THF, reflux, 10 h, 2.) THF, 50 deg C, 2 h

8: 45 percent / 4-(dimethylamino)pyridine, Et₃N / CH₂Cl₂ / 4 h / Ambient temperature

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium hydroxide; lithium borohydride; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; L-(+)-diisopropyl tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; dihydrogen peroxide; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.3891/acta.chem.scand.47-1019