(1S,4S)-3-Benzenesulfonyl-2-[2-((1R,6S)-7,7-dimethyl-bicyclo[4.1.0]hept-2-en-3-yl)-[1,3]dithian-2-yl]-4-methyl-cyclopentanol

Base Information

• Chemical Name: (1S,4S)-3-Benzenesulfonyl-2-[2-((1R,6S)-7,7-dimethyl-bicyclo[4.1.0]hept-2-en-3-yl)-[1,3]dithian-2-yl]-4-methyl-cyclopentanol
• CAS No.: 78012-43-8
• Molecular Formula: C₂₅H₃₄O₃S₃
• Molecular Weight: 478.741
• Mol file: 78012-43-8.mol

Synonyms:

Chemical Property of (1S,4S)-3-Benzenesulfonyl-2-[2-((1R,6S)-7,7-dimethyl-bicyclo[4.1.0]hept-2-en-3-yl)-[1,3]dithian-2-yl]-4-methyl-cyclopentanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4S)-3-Benzenesulfonyl-2-[2-((1R,6S)-7,7-dimethyl-bicyclo[4.1.0]hept-2-en-3-yl)-[1,3]dithian-2-yl]-4-methyl-cyclopentanol

There total 4 articles about (1S,4S)-3-Benzenesulfonyl-2-[2-((1R,6S)-7,7-dimethyl-bicyclo[4.1.0]hept-2-en-3-yl)-[1,3]dithian-2-yl]-4-methyl-cyclopentanol 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: 65.0%

(1R,6S)-7,7-dimethyl-3-(1,3-dithia-2-cyclohexyl)bicyclo<4.1.0>hept-2-ene (78012-41-6) + (1R,4R)-trans-4-methyl-3-(phenylsulfonyl)-2-cyclopenten-1-ol (78087-19-1) → (1S,4S)-3-Benzenesulfonyl-2-[2-((1R,6S)-7,7-dimethyl-bicyclo[4.1.0]hept-2-en-3-yl)-[1,3]dithian-2-yl]-4-methyl-cyclopentanol (78012-43-8,115115-25-8,115115-28-1)

Guidance literature:

With n-butyllithium; methyllithium; In tetrahydrofuran; at -78 ℃;

DOI:10.1021/ja00398a050

Reference yield:

(1R,6S)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxaldehyde (14917-83-0,247911-68-8) → (1S,4S)-3-Benzenesulfonyl-2-[2-((1R,6S)-7,7-dimethyl-bicyclo[4.1.0]hept-2-en-3-yl)-[1,3]dithian-2-yl]-4-methyl-cyclopentanol (78012-43-8,115115-25-8,115115-28-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / boron trifluoride etherate / CH₂Cl₂

2: 65 percent / methyllithium, n-butyllithium / tetrahydrofuran / -78 °C

With n-butyllithium; boron trifluoride diethyl etherate; methyllithium; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00398a050

Reference yield:

(S)-(-)-perillaldehyde (18031-40-8) → (1S,4S)-3-Benzenesulfonyl-2-[2-((1R,6S)-7,7-dimethyl-bicyclo[4.1.0]hept-2-en-3-yl)-[1,3]dithian-2-yl]-4-methyl-cyclopentanol (78012-43-8,115115-25-8,115115-28-1)

Guidance literature:

Multi-step reaction with 4 steps

1: HCl gas / liquid sulphur dioxide / 0.33 h / -45 °C

2: 94 percent / potassium tert-butoxide / tetrahydrofuran / 0 °C

3: 68 percent / boron trifluoride etherate / CH₂Cl₂

4: 65 percent / methyllithium, n-butyllithium / tetrahydrofuran / -78 °C

With hydrogenchloride; n-butyllithium; boron trifluoride diethyl etherate; potassium tert-butylate; methyllithium; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00398a050

upstream raw materials:

(1R,6S)-7,7-dimethyl-3-(1,3-dithia-2-cyclohexyl)bicyclo<4.1.0>hept-2-ene

(1R,4R)-trans-4-methyl-3-(phenylsulfonyl)-2-cyclopenten-1-ol

(1R,6S)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxaldehyde

(S)-(-)-perillaldehyde