(3bS,5aR,9aR,11R)-3b,6,6,9a-Tetramethyl-11-(toluene-4-sulfonyl)-3b,4,5,5a,6,7,8,9,9a,9b,10,11-dodecahydro-phenanthro[1,2-b]furan

Base Information

• Chemical Name: (3bS,5aR,9aR,11R)-3b,6,6,9a-Tetramethyl-11-(toluene-4-sulfonyl)-3b,4,5,5a,6,7,8,9,9a,9b,10,11-dodecahydro-phenanthro[1,2-b]furan
• CAS No.: 105631-27-4
• Molecular Formula: C₂₇H₃₆O₃S
• Molecular Weight: 440.647
• Mol file: 105631-27-4.mol

Synonyms:

Chemical Property of (3bS,5aR,9aR,11R)-3b,6,6,9a-Tetramethyl-11-(toluene-4-sulfonyl)-3b,4,5,5a,6,7,8,9,9a,9b,10,11-dodecahydro-phenanthro[1,2-b]furan

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3bS,5aR,9aR,11R)-3b,6,6,9a-Tetramethyl-11-(toluene-4-sulfonyl)-3b,4,5,5a,6,7,8,9,9a,9b,10,11-dodecahydro-phenanthro[1,2-b]furan

There total 3 articles about (3bS,5aR,9aR,11R)-3b,6,6,9a-Tetramethyl-11-(toluene-4-sulfonyl)-3b,4,5,5a,6,7,8,9,9a,9b,10,11-dodecahydro-phenanthro[1,2-b]furan 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:

farnesyl bromide (24163-93-7,24163-94-8,56881-57-3,6874-67-5,28290-41-7) → (3bS,5aR,9aR,11R)-3b,6,6,9a-Tetramethyl-11-(toluene-4-sulfonyl)-3b,4,5,5a,6,7,8,9,9a,9b,10,11-dodecahydro-phenanthro[1,2-b]furan (105631-27-4)

Guidance literature:

Multi-step reaction with 2 steps

1: n-butyllithium, hexamethylphosphoric triamide (HMPA) / 1.) THF, hexane, 0 deg C, 20 min 2.) THF, hexane, -78 deg C, 1 h

2: 1.) merkury (II) oxide, N,N-dimethylaniline, triflic anhydride, 2.) NaBH₄, NaOH, EtOH, H₂O

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; ethanol; trifluoromethylsulfonic anhydride; water; N,N-dimethyl-aniline; mercury(II) oxide;

DOI:10.1021/jo00231a011

Reference yield:

3-(tosylmethyl)furan (92631-12-4) → (3bS,5aR,9aR,11R)-3b,6,6,9a-Tetramethyl-11-(toluene-4-sulfonyl)-3b,4,5,5a,6,7,8,9,9a,9b,10,11-dodecahydro-phenanthro[1,2-b]furan (105631-27-4)

Guidance literature:

Multi-step reaction with 2 steps

1: n-butyllithium, hexamethylphosphoric triamide (HMPA) / 1.) THF, hexane, 0 deg C, 20 min 2.) THF, hexane, -78 deg C, 1 h

2: 1.) merkury (II) oxide, N,N-dimethylaniline, triflic anhydride, 2.) NaBH₄, NaOH, EtOH, H₂O

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; ethanol; trifluoromethylsulfonic anhydride; water; N,N-dimethyl-aniline; mercury(II) oxide;

DOI:10.1021/jo00231a011

Reference yield:

13-(p-toluenesulfonyl)ambliofuran (105631-15-0) → (3bR,5aS,9aS,9bR,11R)-3b,6,6,9a-Tetramethyl-11-(toluene-4-sulfonyl)-3b,4,5,5a,6,7,8,9,9a,9b,10,11-dodecahydro-phenanthro[1,2-b]furan (105631-26-3) + (3bS,5aR,9aR,11R)-3b,6,6,9a-Tetramethyl-11-(toluene-4-sulfonyl)-3b,4,5,5a,6,7,8,9,9a,9b,10,11-dodecahydro-phenanthro[1,2-b]furan (105631-27-4)

Guidance literature:

With sodium hydroxide; sodium tetrahydroborate; ethanol; trifluoromethylsulfonic anhydride; water; N,N-dimethyl-aniline; mercury(II) oxide; Yield given. Multistep reaction. Yields of byproduct given;

DOI:10.1021/jo00231a011

upstream raw materials:

13-(p-toluenesulfonyl)ambliofuran

farnesyl bromide

3-(tosylmethyl)furan