(4R,5S)-(-)-4-cyclohexyl-4-(4-fluorophenyl)-5-(trimethylsilyl)methyl-1,3-dioxolan-2-one

Base Information

Chemical Name:(4R,5S)-(-)-4-cyclohexyl-4-(4-fluorophenyl)-5-(trimethylsilyl)methyl-1,3-dioxolan-2-one
CAS No.:154808-42-1
Molecular Formula:C₁₉H₂₇FO₃Si
Molecular Weight:350.505
Hs Code.:

Synonyms:(4R,5S)-(-)-4-cyclohexyl-4-(4-fluorophenyl)-5-(trimethylsilyl)methyl-1,3-dioxolan-2-one

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Chemical Property of (4R,5S)-(-)-4-cyclohexyl-4-(4-fluorophenyl)-5-(trimethylsilyl)methyl-1,3-dioxolan-2-one

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Technology Process of (4R,5S)-(-)-4-cyclohexyl-4-(4-fluorophenyl)-5-(trimethylsilyl)methyl-1,3-dioxolan-2-one

There total 9 articles about (4R,5S)-(-)-4-cyclohexyl-4-(4-fluorophenyl)-5-(trimethylsilyl)methyl-1,3-dioxolan-2-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: 63.0%

: 75-44-5
phosgene

: 154808-51-2
(1R,2S)-(+)-1-cyclohexyl-1-(4-fluorophenyl)-3-(trimethylsilyl)propane-1,2-diol

: 154808-42-1
(4R,5S)-(-)-4-cyclohexyl-4-(4-fluorophenyl)-5-(trimethylsilyl)methyl-1,3-dioxolan-2-one

Guidance literature:: With pyridine; In tetrahydrofuran; toluene;
DOI:10.3891/acta.chem.scand.47-1019

Reference yield:

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

: 154808-42-1
(4R,5S)-(-)-4-cyclohexyl-4-(4-fluorophenyl)-5-(trimethylsilyl)methyl-1,3-dioxolan-2-one

Guidance literature:: Multi-step reaction with 6 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

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium borohydride; oxalyl dichloride; L-(+)-diisopropyl tartrate; 4 A molecular sieve; 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

: 154808-42-1
(4R,5S)-(-)-4-cyclohexyl-4-(4-fluorophenyl)-5-(trimethylsilyl)methyl-1,3-dioxolan-2-one

Guidance literature:: Multi-step reaction with 5 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

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium borohydride; oxalyl dichloride; L-(+)-diisopropyl tartrate; 4 A molecular sieve; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.3891/acta.chem.scand.47-1019