(2S,3S)-(+)-3-cyclohexyl-2,3-epoxy-3-phenylpropyl 4-nitrobenzenesulfonate

Base Information

• Chemical Name: (2S,3S)-(+)-3-cyclohexyl-2,3-epoxy-3-phenylpropyl 4-nitrobenzenesulfonate
• CAS No.: 149598-05-0
• Molecular Formula: C₂₁H₂₃NO₆S
• Molecular Weight: 417.483
• Mol file: 149598-05-0.mol

Synonyms:(2S,3S)-(+)-3-cyclohexyl-2,3-epoxy-3-phenylpropyl 4-nitrobenzenesulfonate

Chemical Property of (2S,3S)-(+)-3-cyclohexyl-2,3-epoxy-3-phenylpropyl 4-nitrobenzenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-(+)-3-cyclohexyl-2,3-epoxy-3-phenylpropyl 4-nitrobenzenesulfonate

There total 9 articles about (2S,3S)-(+)-3-cyclohexyl-2,3-epoxy-3-phenylpropyl 4-nitrobenzenesulfonate 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: 90.0%

(+)-(2S,3S)-trans-3-cyclohexyl-3-phenyloxiranemethanol (149598-04-9) + 4-Nitrobenzenesulfonyl chloride (98-74-8) → (2S,3S)-(+)-3-cyclohexyl-2,3-epoxy-3-phenylpropyl 4-nitrobenzenesulfonate (149598-05-0)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 ℃; for 2h;

Reference yield:

Cyclohexyl phenyl ketone (712-50-5) → (2S,3S)-(+)-3-cyclohexyl-2,3-epoxy-3-phenylpropyl 4-nitrobenzenesulfonate (149598-05-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 85 percent / Zn, I₂ / dioxane / 3.25 h / 0 - 20 °C / Irradiation

2: 5.28 g / 15percent aq. KOH / 2.5 h / Heating

4: NaBH₄, BF₃*Et₂O / tetrahydrofuran / Heating

5: 82 percent / Et₃N,4-dimethylaminopyridine (DMAP) / CH₂Cl₂ / 4 h / 0 °C

6: 1.) 2-nitrophenyl selenocyanate, NaBH₄, 2.) 30percent aq. H₂O₂ / 1.) ethanol, RT, 5 h, 2.) THF, ethanol, RT, 18 h

7: 33 percent / 3-chloroperbenzoic acid, NaHCO₃ / CH₂Cl₂ / 36 h

8: 85 percent / t-BuOK / dimethylformamide / 1 h / Ambient temperature

9: 90 percent / Et₃N, DMAP / CH₂Cl₂ / 2 h / 0 °C

With dmap; potassium hydroxide; sodium tetrahydroborate; ortho-nitrophenyl selenocyanate; boron trifluoride diethyl etherate; potassium tert-butylate; dihydrogen peroxide; iodine; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

(+/-)-3-cyclohexyl-3-hydroxy-3-phenylpropanoic acid ethyl ester (26482-37-1) → (2S,3S)-(+)-3-cyclohexyl-2,3-epoxy-3-phenylpropyl 4-nitrobenzenesulfonate (149598-05-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 5.28 g / 15percent aq. KOH / 2.5 h / Heating

3: NaBH₄, BF₃*Et₂O / tetrahydrofuran / Heating

4: 82 percent / Et₃N,4-dimethylaminopyridine (DMAP) / CH₂Cl₂ / 4 h / 0 °C

5: 1.) 2-nitrophenyl selenocyanate, NaBH₄, 2.) 30percent aq. H₂O₂ / 1.) ethanol, RT, 5 h, 2.) THF, ethanol, RT, 18 h

6: 33 percent / 3-chloroperbenzoic acid, NaHCO₃ / CH₂Cl₂ / 36 h

7: 85 percent / t-BuOK / dimethylformamide / 1 h / Ambient temperature

8: 90 percent / Et₃N, DMAP / CH₂Cl₂ / 2 h / 0 °C

With dmap; potassium hydroxide; sodium tetrahydroborate; ortho-nitrophenyl selenocyanate; boron trifluoride diethyl etherate; potassium tert-butylate; dihydrogen peroxide; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

(+)-(2S,3S)-trans-3-cyclohexyl-3-phenyloxiranemethanol

4-Nitrobenzenesulfonyl chloride

Cyclohexyl phenyl ketone

(+/-)-3-cyclohexyl-3-hydroxy-3-phenylpropanoic acid ethyl ester