dithiocarbonic acid O-{2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-isopropenyl-5-methyl-5-vinyl-cyclohexyl} ester S-methyl ester

Base Information

• Chemical Name: dithiocarbonic acid O-{2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-isopropenyl-5-methyl-5-vinyl-cyclohexyl} ester S-methyl ester
• CAS No.: 229010-44-0
• Molecular Formula: C₂₂H₄₀O₂S₂Si
• Molecular Weight: 428.776
• Mol file: 229010-44-0.mol

Synonyms:

Chemical Property of dithiocarbonic acid O-{2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-isopropenyl-5-methyl-5-vinyl-cyclohexyl} ester S-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dithiocarbonic acid O-{2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-isopropenyl-5-methyl-5-vinyl-cyclohexyl} ester S-methyl ester

There total 9 articles about dithiocarbonic acid O-{2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-isopropenyl-5-methyl-5-vinyl-cyclohexyl} ester S-methyl ester 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:

(4R,5R)-1-Acetoxy-4-isopropenyl-5-methyl-5-vinylcyclohex-1-ene (149404-74-0) → dithiocarbonic acid O-{2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-isopropenyl-5-methyl-5-vinyl-cyclohexyl} ester S-methyl ester (229010-44-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / K₂CO₃ / methanol

2: LDA, HMPA / tetrahydrofuran; hexane / 1.) -78 deg C, 30 min, 2.) -78 to -40 deg C, 4 h

3: 81 percent / LiAlH₄ / tetrahydrofuran / 2 h / -50 °C

4: 87 percent / imidazole / dimethylformamide / 1 h

5: 1.) BuLi / 1.) THF, hexane, -78 deg C, 30 min; -78 deg C, 30 min, 2.) THF, hexane, 50 min

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; n-butyllithium; potassium carbonate; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; N,N-dimethyl-formamide;

DOI:10.1039/a809983i

Reference yield:

(3R,4R)-3-Methyl-4-isopropenyl-3-vinylcyclohexanone (149404-72-8) → dithiocarbonic acid O-{2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-isopropenyl-5-methyl-5-vinyl-cyclohexyl} ester S-methyl ester (229010-44-0)

Guidance literature:

Multi-step reaction with 4 steps

1: LDA, HMPA / tetrahydrofuran; hexane / 1.) -78 deg C, 30 min, 2.) -78 to -40 deg C, 4 h

2: 81 percent / LiAlH₄ / tetrahydrofuran / 2 h / -50 °C

3: 87 percent / imidazole / dimethylformamide / 1 h

4: 1.) BuLi / 1.) THF, hexane, -78 deg C, 30 min; -78 deg C, 30 min, 2.) THF, hexane, 50 min

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; n-butyllithium; lithium diisopropyl amide; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

DOI:10.1039/a809983i

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → dithiocarbonic acid O-{2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-isopropenyl-5-methyl-5-vinyl-cyclohexyl} ester S-methyl ester (229010-44-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / imidazole / dimethylformamide / 1 h

2: 1.) BuLi / 1.) THF, hexane, -78 deg C, 30 min; -78 deg C, 30 min, 2.) THF, hexane, 50 min

With 1H-imidazole; n-butyllithium; In N,N-dimethyl-formamide;

DOI:10.1039/a809983i

upstream raw materials:

carbon disulfide

(1S,2S,4R,5R)-2-<2-(tert-Butyldimethylsilyloxy)ethyl>-4-isopropenyl-5-methyl-5-vinylcyclohexanol

methyl iodide

tert-butyldimethylsilyl chloride

Downstream raw materials:

Methyl 2-<(1S,3R,4R)-3-isopropenyl-4-methyl-4-vinylcyclohexyl>-4-<(5R)-2,2,4,4-tetramethyl-1,3-dioxolan-5-yl>butanoate

Methyl (5R)-2-<(1S,3R,4R)-3-isopropenyl-4-methyl-4-vinylcyclohexyl>-5,6-dihydroxy-6-methylheptanoate

Methyl 2-<(1S,3R,4R)-3-isopropenyl-4-methyl-4-vinylcyclohexyl>acetate

2-<(1S,3R,4R)-(3-Isopropenyl-4-methyl-4-vinylcyclohexyl)>ethanol