(+/-)-(1S,3aR,4S,5R,7aS)-1-ethyl-3a,4,5,7a-tetrahydro-5-<(phenylthio)methyl>-4-indancarboxylic acid

Base Information

• Chemical Name: (+/-)-(1S,3aR,4S,5R,7aS)-1-ethyl-3a,4,5,7a-tetrahydro-5-<(phenylthio)methyl>-4-indancarboxylic acid
• CAS No.: 81331-47-7
• Molecular Formula: C₁₉H₂₄O₂S
• Molecular Weight: 316.464
• Mol file: 81331-47-7.mol

Synonyms:

Chemical Property of (+/-)-(1S,3aR,4S,5R,7aS)-1-ethyl-3a,4,5,7a-tetrahydro-5-<(phenylthio)methyl>-4-indancarboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-(1S,3aR,4S,5R,7aS)-1-ethyl-3a,4,5,7a-tetrahydro-5-<(phenylthio)methyl>-4-indancarboxylic acid

There total 12 articles about (+/-)-(1S,3aR,4S,5R,7aS)-1-ethyl-3a,4,5,7a-tetrahydro-5-<(phenylthio)methyl>-4-indancarboxylic acid 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:

lithium thiophenoxide (2973-86-6) + (+/-)-1α-Ethyl-5β-(hydroxymethyl)-3aβ,4,5,7aα-tetrahydroindan-4β-carboxylic Acid γ-Lactone (76566-89-7,88244-69-3,78216-75-8,91109-68-1) → (+/-)-(1S,3aR,4S,5R,7aS)-1-ethyl-3a,4,5,7a-tetrahydro-5-<(phenylthio)methyl>-4-indancarboxylic acid (81331-47-7,95671-28-6)

Guidance literature:

In N,N-dimethyl-formamide; at 110 ℃; for 3h;

DOI:10.1021/ja00413a037 DOI:10.1021/jo00209a017

Reference yield:

3,4,5,6-tetrahydro-2H-pyran-2-one (542-28-9,26354-94-9) → (+/-)-(1S,3aR,4S,5R,7aS)-1-ethyl-3a,4,5,7a-tetrahydro-5-<(phenylthio)methyl>-4-indancarboxylic acid (81331-47-7,95671-28-6)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) LDA, 2.) HMPA / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 6 h

2: 100 percent / diisobutylaluminum hydride / CH₂Cl₂; toluene / 1 h / -78 °C

3: 70 percent / imidazole / dimethylformamide / 1.5 h / 0 - 20 °C

4: 1.) LDA / 1.) THF, hexane, -78 deg C, 10 min, 2.) THF, hexane, from 0 deg C to 25 deg C, 2 h

5: diisobutylaluminum hydride / CH₂Cl₂; tetrahydrofuran / 1 h / -78 °C

6: imidazole / dimethylformamide / 1 h / Ambient temperature

7: aq. AcOH / tetrahydrofuran / 1 h / 25 °C

8: pyridinium chlorochromate / CH₂Cl₂ / 2 h / Ambient temperature

9: toluene / 12 h / 25 °C

10: toluene / 48 h / 130 °C

11: n-Bu₄NF / tetrahydrofuran / Ambient temperature

12: dimethylformamide / 3 h / 110 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; acetic acid; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00209a017

Reference yield:

3-ethyl-tetrahydro-pyran-2-one (32821-68-4,103957-83-1) → (+/-)-(1S,3aR,4S,5R,7aS)-1-ethyl-3a,4,5,7a-tetrahydro-5-<(phenylthio)methyl>-4-indancarboxylic acid (81331-47-7,95671-28-6)

Guidance literature:

Multi-step reaction with 11 steps

1: 100 percent / diisobutylaluminum hydride / CH₂Cl₂; toluene / 1 h / -78 °C

2: 70 percent / imidazole / dimethylformamide / 1.5 h / 0 - 20 °C

3: 1.) LDA / 1.) THF, hexane, -78 deg C, 10 min, 2.) THF, hexane, from 0 deg C to 25 deg C, 2 h

4: diisobutylaluminum hydride / CH₂Cl₂; tetrahydrofuran / 1 h / -78 °C

5: imidazole / dimethylformamide / 1 h / Ambient temperature

6: aq. AcOH / tetrahydrofuran / 1 h / 25 °C

7: pyridinium chlorochromate / CH₂Cl₂ / 2 h / Ambient temperature

8: toluene / 12 h / 25 °C

9: toluene / 48 h / 130 °C

10: n-Bu₄NF / tetrahydrofuran / Ambient temperature

11: dimethylformamide / 3 h / 110 °C

With 1H-imidazole; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; acetic acid; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00209a017

upstream raw materials:

lithium thiophenoxide

(+/-)-1α-Ethyl-5β-(hydroxymethyl)-3aβ,4,5,7aα-tetrahydroindan-4β-carboxylic Acid γ-Lactone

3,4,5,6-tetrahydro-2H-pyran-2-one

3-ethyl-tetrahydro-pyran-2-one

Downstream raw materials:

antibiotic X-14547 A

(R)-2-((2R,5S,6R)-6-{(E)-4-Benzenesulfonyl-4-[(1R,3aS,4R,5S,7aR)-4-(tert-butyl-dimethyl-silanyloxymethyl)-1-ethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl]-1-ethyl-but-1-enyl}-5-methyl-tetrahydro-pyran-2-yl)-propionic acid methyl ester

(R)-2-((2R,5S,6R)-6-{(E)-4-Benzenesulfonyl-4-[(1S,3aR,4S,5R,7aS)-4-(tert-butyl-dimethyl-silanyloxymethyl)-1-ethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl]-1-ethyl-but-1-enyl}-5-methyl-tetrahydro-pyran-2-yl)-propionic acid methyl ester

(+/-)-tert-butyl<<(1S,3aR,4S,5R,7aS)-1-ethyl-3a,4,5,7a-tetrahydro-5-<(phenylsulfonyl)methyl>-4-indanyl>methoxy>dimethylsilane