(1R,4aR,5S,8aS)-5-Hydroxy-1,4a-dimethyl-5-((E)-2-phenylsulfanyl-vinyl)-decahydro-naphthalene-1-carboxylic acid methyl ester

Base Information

• Chemical Name: (1R,4aR,5S,8aS)-5-Hydroxy-1,4a-dimethyl-5-((E)-2-phenylsulfanyl-vinyl)-decahydro-naphthalene-1-carboxylic acid methyl ester
• CAS No.: 391277-80-8
• Molecular Formula: C₂₂H₃₀O₃S
• Molecular Weight: 374.544
• Mol file: 391277-80-8.mol

Synonyms:(1R,4aR,5S,8aS)-5-Hydroxy-1,4a-dimethyl-5-((E)-2-phenylsulfanyl-vinyl)-decahydro-naphthalene-1-carboxylic acid methyl ester

Chemical Property of (1R,4aR,5S,8aS)-5-Hydroxy-1,4a-dimethyl-5-((E)-2-phenylsulfanyl-vinyl)-decahydro-naphthalene-1-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4aR,5S,8aS)-5-Hydroxy-1,4a-dimethyl-5-((E)-2-phenylsulfanyl-vinyl)-decahydro-naphthalene-1-carboxylic acid methyl ester

There total 7 articles about (1R,4aR,5S,8aS)-5-Hydroxy-1,4a-dimethyl-5-((E)-2-phenylsulfanyl-vinyl)-decahydro-naphthalene-1-carboxylic acid 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: 86.0%

thiophenol (108-98-5) + (1R,4aR,5S,8aS)-5-Ethynyl-5-hydroxy-1,4a-dimethyl-decahydro-naphthalene-1-carboxylic acid methyl ester (287401-10-9) → (1R,4aR,5S,8aS)-5-Hydroxy-1,4a-dimethyl-5-((E)-2-phenylsulfanyl-vinyl)-decahydro-naphthalene-1-carboxylic acid methyl ester (391277-80-8)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); In xylene; at 120 ℃; for 18h;

DOI:10.1021/ol0060578

Reference yield:

(R)-Wieland-Miescher ketone (100348-93-4) → (1R,4aR,5S,8aS)-5-Hydroxy-1,4a-dimethyl-5-((E)-2-phenylsulfanyl-vinyl)-decahydro-naphthalene-1-carboxylic acid methyl ester (391277-80-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 90 percent / PTSA / benzene / 4 h / 80 °C

2.1: Li; liq. NH₃ / 2-methyl-propan-2-ol / -78 - -30 °C

2.2: 55 percent / diethyl ether / 2 h / -78 - 0 °C

3.1: NaH / hexamethylphosphoric acid triamide / 3 h / 25 °C

3.2: 95 percent / hexamethylphosphoric acid triamide / 2 h / 25 °C

4.1: Li; liq. NH₃ / 0.33 h / -78 - -30 °C

4.2: 61 percent / 1 h / -78 - -30 °C

5.1: 95 percent / aq. HCl / tetrahydrofuran / 0.25 h / 25 °C

6.1: 91 percent / diethyl ether / 1 h / 25 °C

7.1: 86 percent / AIBN / xylene / 18 h / 120 °C

With hydrogenchloride; 2,2'-azobis(isobutyronitrile); ammonia; lithium; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; xylene; tert-butyl alcohol; benzene; 1.1: ketalization / 2.1: Reduction / 2.2: Condensation / 3.1: deprotonation / 3.2: Alkylation / 4.1: Metallation / 4.2: Methylation / 5.1: Hydrolysis / 6.1: Addition / 7.1: Addition;

DOI:10.1021/ol0060578

Reference yield:

(8aR)-3,4,8,8a-tetrahydro-8a-methyl-1,6(2H,7H)-naphthalenedione 1-ethylene ketal (117556-90-8) → (1R,4aR,5S,8aS)-5-Hydroxy-1,4a-dimethyl-5-((E)-2-phenylsulfanyl-vinyl)-decahydro-naphthalene-1-carboxylic acid methyl ester (391277-80-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: Li; liq. NH₃ / 2-methyl-propan-2-ol / -78 - -30 °C

1.2: 55 percent / diethyl ether / 2 h / -78 - 0 °C

2.1: NaH / hexamethylphosphoric acid triamide / 3 h / 25 °C

2.2: 95 percent / hexamethylphosphoric acid triamide / 2 h / 25 °C

3.1: Li; liq. NH₃ / 0.33 h / -78 - -30 °C

3.2: 61 percent / 1 h / -78 - -30 °C

4.1: 95 percent / aq. HCl / tetrahydrofuran / 0.25 h / 25 °C

5.1: 91 percent / diethyl ether / 1 h / 25 °C

6.1: 86 percent / AIBN / xylene / 18 h / 120 °C

With hydrogenchloride; 2,2'-azobis(isobutyronitrile); ammonia; lithium; sodium hydride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; xylene; tert-butyl alcohol; 1.1: Reduction / 1.2: Condensation / 2.1: deprotonation / 2.2: Alkylation / 3.1: Metallation / 3.2: Methylation / 4.1: Hydrolysis / 5.1: Addition / 6.1: Addition;

DOI:10.1021/ol0060578

upstream raw materials:

thiophenol

(1R,4aR,5S,8aS)-5-Ethynyl-5-hydroxy-1,4a-dimethyl-decahydro-naphthalene-1-carboxylic acid methyl ester

(R)-Wieland-Miescher ketone

(8aR)-3,4,8,8a-tetrahydro-8a-methyl-1,6(2H,7H)-naphthalenedione 1-ethylene ketal

Downstream raw materials:

(1R,4aR,10aS)-7-Formyl-1,4a,7-trimethyl-6-phenylsulfanyl-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydro-phenanthrene-1-carboxylic acid methyl ester

Acanthoic acid

(1R,4aR,8aS)-1,4a-Dimethyl-5-((E)-2-phenylsulfanyl-vinyl)-1,2,3,4,4a,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester