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

Base Information

Chemical Name:(1R,4aR,8aS)-5-Hydroxy-1,4a-dimethyl-5-((E)-2-phenylsulfanyl-vinyl)-decahydro-naphthalene-1-carboxylic acid methyl ester
CAS No.:467222-25-9
Molecular Formula:C₂₂H₃₀O₃S
Molecular Weight:374.544
Hs Code.:

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

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

Chemical Property:

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Technology Process of (1R,4aR,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,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%

: 108-98-5
thiophenol

: 308795-75-7
(1R,4aR,8aS)-5-Ethynyl-5-hydroxy-1,4a-dimethyl-decahydro-naphthalene-1-carboxylic acid methyl ester

: 467222-25-9
(1R,4aR,8aS)-5-Hydroxy-1,4a-dimethyl-5-((E)-2-phenylsulfanyl-vinyl)-decahydro-naphthalene-1-carboxylic acid methyl ester

Guidance literature:: With 2,2'-azobis(isobutyronitrile); In xylene; at 120 ℃; for 18h;
DOI:10.1021/jo0159035

Reference yield:

: 100348-93-4
(R)-Wieland-Miescher ketone

: 467222-25-9
(1R,4aR,8aS)-5-Hydroxy-1,4a-dimethyl-5-((E)-2-phenylsulfanyl-vinyl)-decahydro-naphthalene-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 90 percent / p-TsOH / benzene / 4 h / 80 °C

2.1: Li; tert-butyl alcohol / liquid ammonia; diethyl ether / 0.5 h / -78 - -45 °C

2.2: isoprene / liquid ammonia; diethyl ether / -78 - -45 °C

2.3: 87 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 / liquid ammonia; 1,2-dimethoxy-ethane / 0.33 h / -78 - -33 °C

4.2: 61 percent / 1,2-dimethoxy-ethane; liquid ammonia / 1 h / -78 - -33 °C

5.1: 95 percent / 1 M HCl / tetrahydrofuran / 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); lithium; sodium hydride; toluene-4-sulfonic acid; tert-butyl alcohol; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; diethyl ether; ammonia; xylene; benzene;
DOI:10.1021/jo0159035

Reference yield:

: 117556-90-8
(8aR)-3,4,8,8a-tetrahydro-8a-methyl-1,6(2H,7H)-naphthalenedione 1-ethylene ketal

: 467222-25-9
(1R,4aR,8aS)-5-Hydroxy-1,4a-dimethyl-5-((E)-2-phenylsulfanyl-vinyl)-decahydro-naphthalene-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: Li; tert-butyl alcohol / liquid ammonia; diethyl ether / 0.5 h / -78 - -45 °C

1.2: isoprene / liquid ammonia; diethyl ether / -78 - -45 °C

1.3: 87 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 / liquid ammonia; 1,2-dimethoxy-ethane / 0.33 h / -78 - -33 °C

3.2: 61 percent / 1,2-dimethoxy-ethane; liquid ammonia / 1 h / -78 - -33 °C

4.1: 95 percent / 1 M HCl / tetrahydrofuran / 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); lithium; sodium hydride; tert-butyl alcohol; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; diethyl ether; ammonia; xylene;
DOI:10.1021/jo0159035