(4R)-1-(1,3-dithianyl)-4-(2-propenylepoxy)-2-cyclohexen-1-ol

Base Information

• Chemical Name: (4R)-1-(1,3-dithianyl)-4-(2-propenylepoxy)-2-cyclohexen-1-ol
• CAS No.: 123331-89-5
• Molecular Formula: C₁₃H₂₀O₂S₂
• Molecular Weight: 272.433
• Mol file: 123331-89-5.mol

Synonyms:

Chemical Property of (4R)-1-(1,3-dithianyl)-4-(2-propenylepoxy)-2-cyclohexen-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R)-1-(1,3-dithianyl)-4-(2-propenylepoxy)-2-cyclohexen-1-ol

There total 5 articles about (4R)-1-(1,3-dithianyl)-4-(2-propenylepoxy)-2-cyclohexen-1-ol 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:

L-perillaldehyde (5503-12-8) → (4R)-1-(1,3-dithianyl)-4-(2-propenylepoxy)-2-cyclohexen-1-ol (123331-89-5,123408-94-6,137036-88-5,137036-89-6)

Guidance literature:

Multi-step reaction with 5 steps

1: NEt₃ / CH₂Cl₂ / 1) 0 deg C, 30 min, 2) room temperature, 15 min

2: m-chloroperbenzoic acid, aq. NaHCO₃ / CH₂Cl₂ / 0.5 h / Ambient temperature

3: NaIO₄, HF / H₂O; acetonitrile / 2 h / Ambient temperature

4: 85 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 10 h

5: 1) n-BuLi / 1) hexane, THF, 1.5 h, -35 to -25 deg C, 2) THF, room temperature, 30 min

With sodium periodate; n-butyllithium; hydrogen fluoride; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; water; acetonitrile;

DOI:10.1021/jo00024a031

Reference yield:

tert-Butyl-[(R)-4-isopropenyl-cyclohex-2-en-(E)-ylidenemethoxy]-dimethyl-silane (123331-86-2) → (4R)-1-(1,3-dithianyl)-4-(2-propenylepoxy)-2-cyclohexen-1-ol (123331-89-5,123408-94-6,137036-88-5,137036-89-6)

Guidance literature:

Multi-step reaction with 4 steps

1: m-chloroperbenzoic acid, aq. NaHCO₃ / CH₂Cl₂ / 0.5 h / Ambient temperature

2: NaIO₄, HF / H₂O; acetonitrile / 2 h / Ambient temperature

3: 85 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 10 h

4: 1) n-BuLi / 1) hexane, THF, 1.5 h, -35 to -25 deg C, 2) THF, room temperature, 30 min

With sodium periodate; n-butyllithium; hydrogen fluoride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; water; acetonitrile;

DOI:10.1021/jo00024a031

Reference yield:

(R)-(+)-4-(2-propenyl)-2-cyclohexen-1-one (89002-23-3) → (4R)-1-(1,3-dithianyl)-4-(2-propenylepoxy)-2-cyclohexen-1-ol (123331-89-5,123408-94-6,137036-88-5,137036-89-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 10 h

2: 1) n-BuLi / 1) hexane, THF, 1.5 h, -35 to -25 deg C, 2) THF, room temperature, 30 min

With n-butyllithium; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1021/jo00024a031

upstream raw materials:

1,3 dithiane

(R)-4-(2-Methyl-oxiranyl)-cyclohex-2-enone

L-perillaldehyde

(R)-(+)-4-(2-propenyl)-2-cyclohexen-1-one

Downstream raw materials:

(4R)-1-(1,3-dithianyl)-4-(2-(2-hydroxypropanyl))-2-cyclohexen-1-ol

(+/-)-11-hydroxy-Δ⁹-tetrahydrocannabinol