2-<(1'S,2'R,3'R,4'S')-1'-((tert-butyldimethylsilyl)oxy)-4'-methyl-3'-(phenylsulfonyl)cyclopent-2'-yl>-3-(bis(methylthio)methyl)-(1R,6S)-7,7-dimethylbicyclo<4.1.0>hept-3-ene

Base Information

• Chemical Name: 2-<(1'S,2'R,3'R,4'S')-1'-((tert-butyldimethylsilyl)oxy)-4'-methyl-3'-(phenylsulfonyl)cyclopent-2'-yl>-3-(bis(methylthio)methyl)-(1R,6S)-7,7-dimethylbicyclo<4.1.0>hept-3-ene
• CAS No.: 115047-50-2
• Molecular Formula: C₃₀H₄₈O₃S₃Si
• Molecular Weight: 580.993
• Mol file: 115047-50-2.mol

Synonyms:

Chemical Property of 2-<(1'S,2'R,3'R,4'S')-1'-((tert-butyldimethylsilyl)oxy)-4'-methyl-3'-(phenylsulfonyl)cyclopent-2'-yl>-3-(bis(methylthio)methyl)-(1R,6S)-7,7-dimethylbicyclo<4.1.0>hept-3-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-<(1'S,2'R,3'R,4'S')-1'-((tert-butyldimethylsilyl)oxy)-4'-methyl-3'-(phenylsulfonyl)cyclopent-2'-yl>-3-(bis(methylthio)methyl)-(1R,6S)-7,7-dimethylbicyclo<4.1.0>hept-3-ene

There total 5 articles about 2-<(1'S,2'R,3'R,4'S')-1'-((tert-butyldimethylsilyl)oxy)-4'-methyl-3'-(phenylsulfonyl)cyclopent-2'-yl>-3-(bis(methylthio)methyl)-(1R,6S)-7,7-dimethylbicyclo<4.1.0>hept-3-ene 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:

(S)-(-)-perillaldehyde (18031-40-8) → 2-<(1'S,2'R,3'R,4'S')-1'-((tert-butyldimethylsilyl)oxy)-4'-methyl-3'-(phenylsulfonyl)cyclopent-2'-yl>-3-(bis(methylthio)methyl)-(1R,6S)-7,7-dimethylbicyclo<4.1.0>hept-3-ene (115047-50-2)

Guidance literature:

Multi-step reaction with 4 steps

1: sulfur dioxide, hydrogen chloride (gas) / 0.67 h / -45 °C

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

3: 70 percent / TiCl₄ / 0.17 h / -78 °C

4: 1.) lithium diisopropylamide (LDA), HMPA / 1.) THF, 30 min, 2.) 15 min

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sulfur dioxide; potassium tert-butylate; titanium tetrachloride; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1021/jo00251a001

Reference yield:

(4S)-4-(1-chloro-1-methylethyl)-1-cyclohexenecarboxaldehyde (78012-40-5) → 2-<(1'S,2'R,3'R,4'S')-1'-((tert-butyldimethylsilyl)oxy)-4'-methyl-3'-(phenylsulfonyl)cyclopent-2'-yl>-3-(bis(methylthio)methyl)-(1R,6S)-7,7-dimethylbicyclo<4.1.0>hept-3-ene (115047-50-2)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium tert-butoxide / tetrahydrofuran / 0 °C

2: 70 percent / TiCl₄ / 0.17 h / -78 °C

3: 1.) lithium diisopropylamide (LDA), HMPA / 1.) THF, 30 min, 2.) 15 min

With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium tert-butylate; titanium tetrachloride; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1021/jo00251a001

Reference yield:

(1R,6S)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxaldehyde (14917-83-0,247911-68-8) → 2-<(1'S,2'R,3'R,4'S')-1'-((tert-butyldimethylsilyl)oxy)-4'-methyl-3'-(phenylsulfonyl)cyclopent-2'-yl>-3-(bis(methylthio)methyl)-(1R,6S)-7,7-dimethylbicyclo<4.1.0>hept-3-ene (115047-50-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / TiCl₄ / 0.17 h / -78 °C

2: 1.) lithium diisopropylamide (LDA), HMPA / 1.) THF, 30 min, 2.) 15 min

With N,N,N,N,N,N-hexamethylphosphoric triamide; titanium tetrachloride; lithium diisopropyl amide;

DOI:10.1021/jo00251a001

upstream raw materials:

(1R,6S)-7,7-dimethyl-3-(bis(methylthio)methyl)bicyclo<4.1.0>hept-2-ene

((1S,4S)-3-Benzenesulfonyl-4-methyl-cyclopent-2-enyloxy)-tert-butyl-dimethyl-silane

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

(S)-(-)-perillaldehyde