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

Base Information

• Chemical Name: (+)-(2S,3S)-trans-3-cyclohexyl-3-phenyloxiranemethanol
• CAS No.: 149598-04-9
• Molecular Formula: C₁₅H₂₀O₂
• Molecular Weight: 232.323
• Mol file: 149598-04-9.mol

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

Chemical Property of (+)-(2S,3S)-trans-3-cyclohexyl-3-phenyloxiranemethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(2S,3S)-trans-3-cyclohexyl-3-phenyloxiranemethanol

There total 9 articles about (+)-(2S,3S)-trans-3-cyclohexyl-3-phenyloxiranemethanol 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: 85.0%

(1S,2R)-(+)-1-cyclohexyl-2,3-epoxy-1-phenyl-1-propanol (149632-19-9) → (+)-(2S,3S)-trans-3-cyclohexyl-3-phenyloxiranemethanol (149598-04-9)

Guidance literature:

With potassium tert-butylate; In N,N-dimethyl-formamide; for 1h; Ambient temperature;

Reference yield: 80.0%

(2E)-3-cyclohexyl-3-phenylprop-2-en-1-ol (462093-58-9) → (+)-(2S,3S)-trans-3-cyclohexyl-3-phenyloxiranemethanol (149598-04-9)

Guidance literature:

With Oxone; C₂₈H₃₆N⁽¹⁺⁾*F₆Sb^(1-); sodium hydrogencarbonate; In water; acetonitrile; at 0 ℃; for 24h; optical yield given as %ee; enantioselective reaction;

DOI:10.1016/j.tetasy.2010.06.002

Reference yield:

Cyclohexyl phenyl ketone (712-50-5) → (+)-(2S,3S)-trans-3-cyclohexyl-3-phenyloxiranemethanol (149598-04-9)

Guidance literature:

Multi-step reaction with 8 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

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;

upstream raw materials:

(1S,2R)-(+)-1-cyclohexyl-2,3-epoxy-1-phenyl-1-propanol

Cyclohexyl phenyl ketone

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

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

Downstream raw materials:

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