(1S,4aR,8aS)-6-[1-Methoxy-1-phenylsulfanyl-meth-(Z)-ylidene]-8a-methyl-4-methylene-decahydro-naphthalen-1-ol

Base Information

• Chemical Name: (1S,4aR,8aS)-6-[1-Methoxy-1-phenylsulfanyl-meth-(Z)-ylidene]-8a-methyl-4-methylene-decahydro-naphthalen-1-ol
• CAS No.: 87262-45-1
• Molecular Formula: C₂₀H₂₆O₂S
• Molecular Weight: 330.491
• Mol file: 87262-45-1.mol

Synonyms:

Chemical Property of (1S,4aR,8aS)-6-[1-Methoxy-1-phenylsulfanyl-meth-(Z)-ylidene]-8a-methyl-4-methylene-decahydro-naphthalen-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4aR,8aS)-6-[1-Methoxy-1-phenylsulfanyl-meth-(Z)-ylidene]-8a-methyl-4-methylene-decahydro-naphthalen-1-ol

There total 10 articles about (1S,4aR,8aS)-6-[1-Methoxy-1-phenylsulfanyl-meth-(Z)-ylidene]-8a-methyl-4-methylene-decahydro-naphthalen-1-ol 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: 87.0%

lithium (87262-37-1) + 5β-Hydroxy-4aβ-methyl-8-methylene-3,4,4a,5,6,7,8,8aα-octahydronaphthalen-2(1H)-one (87262-36-0) → (1S,4aR,8aS)-6-[1-Methoxy-1-phenylsulfanyl-meth-(Z)-ylidene]-8a-methyl-4-methylene-decahydro-naphthalen-1-ol (87262-45-1,87262-46-2)

Guidance literature:

In tetrahydrofuran; 1) -80 degC, 1 h, 2) warm to room temp.;

DOI:10.1021/jo00171a045

Reference yield:

acetic acid (1S*,8aS*)-(+/-)-8a-methyl-6-oxo-1,2,3,4,6,7,8,8a-octahydronaphthalen-1-yl ester (32042-78-7) → (1S,4aR,8aS)-6-[1-Methoxy-1-phenylsulfanyl-meth-(Z)-ylidene]-8a-methyl-4-methylene-decahydro-naphthalen-1-ol (87262-45-1,87262-46-2)

Guidance literature:

Multi-step reaction with 8 steps

1: conc. sulfuric acid

2: 1) 85percent MCPBA / dioxane / 1) buffer (pH 8), 0 degC, 1 h, 2) 24 h, room temp.

3: 98 percent / conc. HBr / diethyl ether; CH₂Cl₂ / 1 h / Ambient temperature

4: 88 percent / 1) p-TsOH*H₂O, 2) Et₃N / CH₂Cl₂ / Ambient temperature; 1) 45 min

5: 95 percent / NaOMe / methanol / 22 h

6: dimethylsulfinylsodium / dimethylsulfoxide / 20 h / Ambient temperature

7: conc HCl / acetone / 1.5 h / Ambient temperature

8: 87 percent / tetrahydrofuran / 1) -80 degC, 1 h, 2) warm to room temp.

With hydrogenchloride; sulfuric acid; dimsylsodium; hydrogen bromide; sodium methylate; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; acetone;

DOI:10.1021/jo00171a045

Reference yield:

4β-Hydroxy-4aβ-methyl-3,4,4a,5,6,8aα-hexahydronaphthalene-1(2H),7(8H)-dione 7-dimethyl acetal (87262-05-3) → (1S,4aR,8aS)-6-[1-Methoxy-1-phenylsulfanyl-meth-(Z)-ylidene]-8a-methyl-4-methylene-decahydro-naphthalen-1-ol (87262-45-1,87262-46-2)

Guidance literature:

Multi-step reaction with 3 steps

1: dimethylsulfinylsodium / dimethylsulfoxide / 20 h / Ambient temperature

2: conc HCl / acetone / 1.5 h / Ambient temperature

3: 87 percent / tetrahydrofuran / 1) -80 degC, 1 h, 2) warm to room temp.

With hydrogenchloride; dimsylsodium; In tetrahydrofuran; dimethyl sulfoxide; acetone;

DOI:10.1021/jo00171a045

upstream raw materials:

lithium

5β-Hydroxy-4aβ-methyl-8-methylene-3,4,4a,5,6,7,8,8aα-octahydronaphthalen-2(1H)-one

4β-Hydroxy-4aβ-methyl-3,4,4a,5,6,8aα-hexahydronaphthalene-1(2H),7(8H)-dione 7-dimethyl acetal

5β-Acetoxy-2-ethoxy-4aβ-methyl-3,4,4a,5,6,7-hexahydronaphthalene

Refernces