(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

Base Information

Chemical Name:(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
CAS No.:287478-47-1
Molecular Formula:C₂₆H₃₄O₃S
Molecular Weight:426.62
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 10 articles about (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 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: 84.0%

: 78-85-3,25120-30-3
2-methylpropenal

: 287401-06-3
(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

: 287478-47-1
(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

Guidance literature:: With tin(IV) chloride; In dichloromethane; at -20 - 0 ℃; for 20h;
DOI:10.1021/jo0159035

Reference yield:

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

: 287478-47-1
(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

Guidance literature:: Multi-step reaction with 9 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

8.1: POCl₃ / hexamethylphosphoric acid triamide / 1 h / 25 °C

8.2: 81 percent / pyridine / hexamethylphosphoric acid triamide / 18 h / 150 °C

9.1: 84 percent / SnCl₄ / CH₂Cl₂ / 20 h / -20 - 0 °C

With hydrogenchloride; 2,2'-azobis(isobutyronitrile); tin(IV) chloride; lithium; sodium hydride; toluene-4-sulfonic acid; tert-butyl alcohol; trichlorophosphate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; diethyl ether; dichloromethane; ammonia; xylene; benzene; 9.1: Diels-Alder cycloaddition;
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

: 287478-47-1
(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

Guidance literature:: Multi-step reaction with 8 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

7.1: POCl₃ / hexamethylphosphoric acid triamide / 1 h / 25 °C

7.2: 81 percent / pyridine / hexamethylphosphoric acid triamide / 18 h / 150 °C

8.1: 84 percent / SnCl₄ / CH₂Cl₂ / 20 h / -20 - 0 °C

With hydrogenchloride; 2,2'-azobis(isobutyronitrile); tin(IV) chloride; lithium; sodium hydride; tert-butyl alcohol; trichlorophosphate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; diethyl ether; dichloromethane; ammonia; xylene; 8.1: Diels-Alder cycloaddition;
DOI:10.1021/jo0159035