Thiocarbonic acid O-((3aS,5aR,6S,8aR)-1,2,3a,6-tetramethyl-4-oxo-decahydro-cyclopenta[c]pentalen-3-yl) ester O-p-tolyl ester

Base Information

• Chemical Name: Thiocarbonic acid O-((3aS,5aR,6S,8aR)-1,2,3a,6-tetramethyl-4-oxo-decahydro-cyclopenta[c]pentalen-3-yl) ester O-p-tolyl ester
• CAS No.: 141193-95-5
• Molecular Formula: C₂₃H₃₀O₃S
• Molecular Weight: 386.555
• Mol file: 141193-95-5.mol

Synonyms:

Chemical Property of Thiocarbonic acid O-((3aS,5aR,6S,8aR)-1,2,3a,6-tetramethyl-4-oxo-decahydro-cyclopenta[c]pentalen-3-yl) ester O-p-tolyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Thiocarbonic acid O-((3aS,5aR,6S,8aR)-1,2,3a,6-tetramethyl-4-oxo-decahydro-cyclopenta[c]pentalen-3-yl) ester O-p-tolyl ester

There total 7 articles about Thiocarbonic acid O-((3aS,5aR,6S,8aR)-1,2,3a,6-tetramethyl-4-oxo-decahydro-cyclopenta[c]pentalen-3-yl) ester O-p-tolyl 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: 6.8%

p-Tolyl chlorothionoformate (937-63-3) + (1SR,5SR,8RS,9RS)-4-hydroxy-2,3,5,9-tetramethyltricyclo<6.3.0.01.5>undecan-6-one (124867-92-1) → Thiocarbonic acid O-((3aS,5aR,6S,8aR)-1,2,3a,6-tetramethyl-4-oxo-decahydro-cyclopenta[c]pentalen-3-yl) ester O-p-tolyl ester (124867-96-5,141193-95-5,141193-96-6,141193-97-7,141195-84-8)

Guidance literature:

With pyridine; In tetrahydrofuran; for 12h; Ambient temperature;

Reference yield:

2-Methylcyclopentanone (1120-72-5) → Thiocarbonic acid O-((3aS,5aR,6S,8aR)-1,2,3a,6-tetramethyl-4-oxo-decahydro-cyclopenta[c]pentalen-3-yl) ester O-p-tolyl ester (124867-96-5,141193-95-5,141193-96-6,141193-97-7,141195-84-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) pyrrolidine / 1.) benzene, 16 h. 2.) toluene, 2 h. reflux

2: KOH / ethanol; H₂O

3: 1.) Mg, BrCH₂CH₂Br 2.) HMPA, TMSCl, CuBr*Me₂S / 1.) ether 2.) ether, -78 gradC, 20 h.

4: 74 percent / HCl / acetone / 120 h / Ambient temperature

5: pyridine / tetrahydrofuran / 16 h / Ambient temperature

With pyrrolidine; pyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex; magnesium; ethylene dibromide; In tetrahydrofuran; ethanol; water; acetone;

DOI:10.1016/S0040-4039(01)80402-0

Reference yield:

2-methylbut-2-enal (497-03-0) → Thiocarbonic acid O-((3aS,5aR,6S,8aR)-1,2,3a,6-tetramethyl-4-oxo-decahydro-cyclopenta[c]pentalen-3-yl) ester O-p-tolyl ester (124867-96-5,141193-95-5,141193-96-6,141193-97-7,141195-84-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) TMSCl, NaI / 1.) MeCN, r.t., 15 min. 2.) r.t., 30 min

2: 1.) Mg, BrCH₂CH₂Br 2.) HMPA, TMSCl, CuBr*Me₂S / 1.) ether 2.) ether, -78 gradC, 20 h.

3: 74 percent / HCl / acetone / 120 h / Ambient temperature

4: pyridine / tetrahydrofuran / 16 h / Ambient temperature

With pyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex; magnesium; ethylene dibromide; sodium iodide; In tetrahydrofuran; acetone;

DOI:10.1016/S0040-4039(01)80402-0

upstream raw materials:

p-Tolyl chlorothionoformate

(1SR,5SR,8RS,9RS)-4-hydroxy-2,3,5,9-tetramethyltricyclo<6.3.0.0^1.5>undecan-6-one

2-Methylcyclopentanone

2-methylbut-2-enal

Downstream raw materials:

p-cresol

rac-silphiperfol-5-en-3-one