(E)-(1R,3aR,7S,8S,10S,12aS)-1-Isopropyl-3a,6,10-trimethyl-8-(toluene-4-sulfonyl)-1,2,3,3a,4,7,8,9,10,11,12,12a-dodecahydro-cyclopentacycloundecen-7-ol

Base Information

• Chemical Name: (E)-(1R,3aR,7S,8S,10S,12aS)-1-Isopropyl-3a,6,10-trimethyl-8-(toluene-4-sulfonyl)-1,2,3,3a,4,7,8,9,10,11,12,12a-dodecahydro-cyclopentacycloundecen-7-ol
• CAS No.: 155157-75-8
• Molecular Formula: C₂₇H₄₂O₃S
• Molecular Weight: 446.695
• Mol file: 155157-75-8.mol

Synonyms:(E)-(1R,3aR,7S,8S,10S,12aS)-1-Isopropyl-3a,6,10-trimethyl-8-(toluene-4-sulfonyl)-1,2,3,3a,4,7,8,9,10,11,12,12a-dodecahydro-cyclopentacycloundecen-7-ol

Chemical Property of (E)-(1R,3aR,7S,8S,10S,12aS)-1-Isopropyl-3a,6,10-trimethyl-8-(toluene-4-sulfonyl)-1,2,3,3a,4,7,8,9,10,11,12,12a-dodecahydro-cyclopentacycloundecen-7-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(1R,3aR,7S,8S,10S,12aS)-1-Isopropyl-3a,6,10-trimethyl-8-(toluene-4-sulfonyl)-1,2,3,3a,4,7,8,9,10,11,12,12a-dodecahydro-cyclopentacycloundecen-7-ol

There total 12 articles about (E)-(1R,3aR,7S,8S,10S,12aS)-1-Isopropyl-3a,6,10-trimethyl-8-(toluene-4-sulfonyl)-1,2,3,3a,4,7,8,9,10,11,12,12a-dodecahydro-cyclopentacycloundecen-7-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:

(E)-4-{(1R,2S,3R)-3-Isopropyl-1-methyl-2-[(S)-3-methyl-5-(toluene-4-sulfonyl)-pentyl]-cyclopentyl}-2-methyl-but-2-enal (933769-62-1) → (E)-(1R,3aR,7S,8R,10S,12aS)-1-Isopropyl-3a,6,10-trimethyl-8-(toluene-4-sulfonyl)-1,2,3,3a,4,7,8,9,10,11,12,12a-dodecahydro-cyclopentacycloundecen-7-ol (155157-78-1) + (E)-(1R,3aR,7S,8S,10S,12aS)-1-Isopropyl-3a,6,10-trimethyl-8-(toluene-4-sulfonyl)-1,2,3,3a,4,7,8,9,10,11,12,12a-dodecahydro-cyclopentacycloundecen-7-ol (155157-75-8)

Guidance literature:

With sodium tert-pentoxide; In benzene; at 35 ℃; for 0.0222222h; Yield given;

DOI:10.1016/S0040-4039(00)61504-6

Reference yield:

C19H36O4 → (E)-(1R,3aR,7S,8S,10S,12aS)-1-Isopropyl-3a,6,10-trimethyl-8-(toluene-4-sulfonyl)-1,2,3,3a,4,7,8,9,10,11,12,12a-dodecahydro-cyclopentacycloundecen-7-ol (155157-75-8)

Guidance literature:

Multi-step reaction with 12 steps

1: CH₃CH₂COOH / 145 °C

2: LiBH₄ / methanol

3: 97 percent / sodium; hexamethylphosphoramide / 2-methyl-propan-2-ol

4: 89 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂

5: NaI / butan-2-one / Heating

6: dimethylformamide / 70 °C

7: 85 percent / HBF₄ / methanol; H₂O

8: (COCl)2; dimethyl sulfoxide; triethylamine / -78 °C

9: 96 percent / CH₂Cl₂ / 22 °C

10: diisobutylaluminum hydride / CH₂Cl₂ / -78 °C

11: pyridinium chlorochromate / CH₂Cl₂

12: sodium tert-amylate / benzene / 0.08 h / 35 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium borohydride; tetrafluoroboric acid; oxalyl dichloride; sodium; sodium tert-pentoxide; diisobutylaluminium hydride; dimethyl sulfoxide; propionic acid; triethylamine; pyridinium chlorochromate; sodium iodide; In methanol; dichloromethane; water; N,N-dimethyl-formamide; butanone; tert-butyl alcohol; benzene; 8: Swern oxidation / 9: Wittig olefination;

DOI:10.1002/anie.200603853

Reference yield:

C21H42O4 (933769-56-3) → (E)-(1R,3aR,7S,8S,10S,12aS)-1-Isopropyl-3a,6,10-trimethyl-8-(toluene-4-sulfonyl)-1,2,3,3a,4,7,8,9,10,11,12,12a-dodecahydro-cyclopentacycloundecen-7-ol (155157-75-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 89 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂

2: NaI / butan-2-one / Heating

3: dimethylformamide / 70 °C

4: 85 percent / HBF₄ / methanol; H₂O

5: (COCl)2; dimethyl sulfoxide; triethylamine / -78 °C

6: 96 percent / CH₂Cl₂ / 22 °C

7: diisobutylaluminum hydride / CH₂Cl₂ / -78 °C

8: pyridinium chlorochromate / CH₂Cl₂

9: sodium tert-amylate / benzene / 0.08 h / 35 °C

With dmap; tetrafluoroboric acid; oxalyl dichloride; sodium tert-pentoxide; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate; sodium iodide; In methanol; dichloromethane; water; N,N-dimethyl-formamide; butanone; benzene; 5: Swern oxidation / 6: Wittig olefination;

DOI:10.1002/anie.200603853

upstream raw materials:

(E)-4-{(1R,2S,3R)-3-Isopropyl-1-methyl-2-[(S)-3-methyl-5-(toluene-4-sulfonyl)-pentyl]-cyclopentyl}-2-methyl-but-2-enal

C₂₁H₄₀O₄

C₂₁H₄₂O₄

C₂₈H₄₈O₆S

Downstream raw materials:

(E)-(1R,3aR,8S,10S,12aS)-1-Isopropyl-3a,6,10-trimethyl-8-(toluene-4-sulfonyl)-2,3,3a,4,8,9,10,11,12,12a-decahydro-1H-cyclopentacycloundecen-7-one