(3aR,4R,7aR)-5,5-(ethylenedioxy)-1-<(phenylthio)methylene>-4-(4-methylpentyl)-3a,4,5,6,7,7a-hexahydro-7a-methylindan

Base Information

• Chemical Name: (3aR,4R,7aR)-5,5-(ethylenedioxy)-1-<(phenylthio)methylene>-4-(4-methylpentyl)-3a,4,5,6,7,7a-hexahydro-7a-methylindan
• CAS No.: 96843-36-6
• Molecular Formula: C₂₅H₃₆O₂S
• Molecular Weight: 400.626
• Mol file: 96843-36-6.mol

Synonyms:

Chemical Property of (3aR,4R,7aR)-5,5-(ethylenedioxy)-1-<(phenylthio)methylene>-4-(4-methylpentyl)-3a,4,5,6,7,7a-hexahydro-7a-methylindan

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4R,7aR)-5,5-(ethylenedioxy)-1-<(phenylthio)methylene>-4-(4-methylpentyl)-3a,4,5,6,7,7a-hexahydro-7a-methylindan

There total 9 articles about (3aR,4R,7aR)-5,5-(ethylenedioxy)-1-<(phenylthio)methylene>-4-(4-methylpentyl)-3a,4,5,6,7,7a-hexahydro-7a-methylindan 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: 95.0%

diethyl [(phenylthio)methyl]phosphonate (38066-16-9) + (-)-(3a,4R,7aR)-5,5-(ethylenedioxy)-4-(4-methylpentyl)-3a,4,5,6,7,7a-hexahydro-7a-methylindan-1-one (96843-35-5) → (3aR,4R,7aR)-5,5-(ethylenedioxy)-1-<(phenylthio)methylene>-4-(4-methylpentyl)-3a,4,5,6,7,7a-hexahydro-7a-methylindan (96843-36-6,96894-95-0)

Guidance literature:

With sodium hydride; In tetrahydrofuran; for 5h; Heating;

DOI:10.1246/cl.1985.259

Reference yield:

(R)-7a-methyl-2,3,7,7a-tetrahydro-6H-indene-1,5-dione (17553-86-5,19576-08-0,20007-98-1,17553-89-8) → (3aR,4R,7aR)-5,5-(ethylenedioxy)-1-<(phenylthio)methylene>-4-(4-methylpentyl)-3a,4,5,6,7,7a-hexahydro-7a-methylindan (96843-36-6,96894-95-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) triethanolamine, 60 deg C, 20 min, 2.) triethanolamine, 60 deg C, 24 h

2: 88 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 3 h / Ambient temperature

3: 71 percent / HCl, H₂ / 5percent Pd/C / acetic acid; methanol / 4 h / Ambient temperature

4: 98 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / benzene / 0.5 h / Ambient temperature

5: 1.) CuI, BF₃*Et₂O / 1.) THF, a) -30 deg C, 30 min, b) RT, 5 min, 2.) THF, RT, 10 min

6: 85 percent / p-toluenesulfonic acid / benzene / 1.5 h / Heating

7: 1.) NaH / 1.) THF, reflux, 30 min, 2.) THF, reflux, 5 h

With hydrogenchloride; copper(l) iodide; boron trifluoride diethyl etherate; hydrogen; sodium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In methanol; dichloromethane; acetic acid; benzene;

DOI:10.1021/jo00376a049

Reference yield:

(-)-(7aR)-4-<(phenylthio)methyl>-5,6,7,7a-tetrahydro-7a-methylindan-1,5-dione (105764-24-7) → (3aR,4R,7aR)-5,5-(ethylenedioxy)-1-<(phenylthio)methylene>-4-(4-methylpentyl)-3a,4,5,6,7,7a-hexahydro-7a-methylindan (96843-36-6,96894-95-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 88 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 3 h / Ambient temperature

2: 71 percent / HCl, H₂ / 5percent Pd/C / acetic acid; methanol / 4 h / Ambient temperature

3: 98 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / benzene / 0.5 h / Ambient temperature

4: 1.) CuI, BF₃*Et₂O / 1.) THF, a) -30 deg C, 30 min, b) RT, 5 min, 2.) THF, RT, 10 min

5: 85 percent / p-toluenesulfonic acid / benzene / 1.5 h / Heating

6: 1.) NaH / 1.) THF, reflux, 30 min, 2.) THF, reflux, 5 h

With hydrogenchloride; copper(l) iodide; boron trifluoride diethyl etherate; hydrogen; sodium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In methanol; dichloromethane; acetic acid; benzene;

DOI:10.1021/jo00376a049

upstream raw materials:

diethyl [(phenylthio)methyl]phosphonate

(-)-(3a,4R,7aR)-5,5-(ethylenedioxy)-4-(4-methylpentyl)-3a,4,5,6,7,7a-hexahydro-7a-methylindan-1-one

(R)-7a-methyl-2,3,7,7a-tetrahydro-6H-indene-1,5-dione

(3-methylbutyl)magnesium bromide

Downstream raw materials:

(-)-<1(S)-methyl-2(S)-((phenylsulfonyl)methyl)-5(R)-(1(S)-((tosyloxy)methyl)-5-methylhexyl)cyclopentyl>acetaldehyde ethylene acetal

(+)-6-methyl-2(R)-<2-((2,5-dioxacyclopentyl)methyl)-2(S)-methyl-3(S)-((phenylsulfonyl)methyl)-1(R)-cyclopentyl>heptanoic acid

(-)-2(S)-methyl-2-<3-(mesyloxy)propyl>-1(S)-<(phenylsulfonyl)methyl>-3(R)-(1(R),5-dimethylhexyl)cyclopentane

(+)-<1(S)-methyl-2(S)-((phenylsulfonyl)methyl)-5(R)-(1(S)-(hydroxymethyl)-5-methylhexyl)cyclopentyl>acetaldehyde ethylene acetal

Refernces

• 1、 Nemoto, Hideo,Kurobe, Hiroshi,Fukomoto, Keiichiro,Kametani, Tetsuji. "A GENERAL METHOD FOR THE STEREOSELECTIVE CONSTRUCTION OF DES-AB-CHOLESTANES. A FIRST TOTAL SYNTHESIS OF (+)-8α-PHENYLSULFONYL-DES-AB-CHOLESTANE". . p. 259 - 262. Retrieved 2007/10/02.