(2S,3R)-4-cyclohexyl-2,3-epoxy-1-butanol

Base Information

• Chemical Name: (2S,3R)-4-cyclohexyl-2,3-epoxy-1-butanol
• CAS No.: 158341-15-2
• Molecular Formula: C₁₀H₁₈O₂
• Molecular Weight: 170.252
• Mol file: 158341-15-2.mol

Synonyms:(2S,3R)-4-cyclohexyl-2,3-epoxy-1-butanol

Chemical Property of (2S,3R)-4-cyclohexyl-2,3-epoxy-1-butanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-4-cyclohexyl-2,3-epoxy-1-butanol

There total 5 articles about (2S,3R)-4-cyclohexyl-2,3-epoxy-1-butanol 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: 59.0%

(2Z)-4-cyclohexyl-1-hydroxy-2-butene (119624-68-9) → (2S,3R)-4-cyclohexyl-2,3-epoxy-1-butanol (158341-15-2)

Guidance literature:

With titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; 4 A molecular sieve; In dichloromethane; toluene; at -20 ℃; for 50h;

DOI:10.1016/S0040-4020(01)80638-4

Reference yield:

cyclohexylethan-1-ol (4442-79-9) → (2S,3R)-4-cyclohexyl-2,3-epoxy-1-butanol (158341-15-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 2,2,6,6-tetramethylpiperidinyloxy free radical (TEMPO), sodium bromide, sodium bicarbonate/5percent bleach / CH₂Cl₂; H₂O / 0.5 h

2: triphenylphosphine / CH₂Cl₂; H₂O / 0.5 h / below 30 deg C

3: 97 percent / 1.) butyllithium / hexane; tetrahydrofuran / 0.5 h / Ambient temperature; 1.) below 0 deg C, 30 min

4: 98 percent / hydrogen / Pd/BaSO₄ / hexane / 0.83 h / 258.6 Torr

5: 59 percent / 4A molecular sieves, titanium(IV) tetrakis(isopropoxide), (R,R)-diisopropyltartrate, tert-butyl hydroperoxide / CH₂Cl₂; toluene / 50 h / -20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hypochlorite; n-butyllithium; 4-oxo-2,2,6,6-tetramethylpiperidin-oxyl; L-(+)-diisopropyl tartrate; 4 A molecular sieve; hydrogen; sodium hydrogencarbonate; triphenylphosphine; sodium bromide; Pd-BaSO₄; In tetrahydrofuran; hexane; dichloromethane; water; toluene;

DOI:10.1016/S0040-4020(01)80638-4

Reference yield:

4-cyclohexyl-1-hydroxy-2-butyne (34452-39-6) → (2S,3R)-4-cyclohexyl-2,3-epoxy-1-butanol (158341-15-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / hydrogen / Pd/BaSO₄ / hexane / 0.83 h / 258.6 Torr

2: 59 percent / 4A molecular sieves, titanium(IV) tetrakis(isopropoxide), (R,R)-diisopropyltartrate, tert-butyl hydroperoxide / CH₂Cl₂; toluene / 50 h / -20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; 4 A molecular sieve; hydrogen; Pd-BaSO₄; In hexane; dichloromethane; toluene;

DOI:10.1016/S0040-4020(01)80638-4

upstream raw materials:

(2Z)-4-cyclohexyl-1-hydroxy-2-butene

cyclohexylethan-1-ol

4-cyclohexyl-1-hydroxy-2-butyne

cyclohexylacetaldehyde

Downstream raw materials:

(2R,3S)-4-cyclohexyl-2,3-epoxybutanal

(2R,3S,4R)-2-bromo-1-cyclohexyl-6-methylheptane-3,4-diol