[(1R,3aR,7aR)-1-[(2S)-1-iodopropan-2-yl]-7a-methyl-1,2,3,3a,6,7-hexahydroinden-4-yl] trifluoromethanesulfonate

Base Information

• Chemical Name: [(1R,3aR,7aR)-1-[(2S)-1-iodopropan-2-yl]-7a-methyl-1,2,3,3a,6,7-hexahydroinden-4-yl] trifluoromethanesulfonate
• CAS No.: 145372-33-4
• Molecular Formula: C14H20F3IO3S
• Molecular Weight: 452.277
• Mol file: 145372-33-4.mol

Synonyms:

Chemical Property of [(1R,3aR,7aR)-1-[(2S)-1-iodopropan-2-yl]-7a-methyl-1,2,3,3a,6,7-hexahydroinden-4-yl] trifluoromethanesulfonate

Chemical Property:

• PSA: 51.75000
• LogP: 5.71470
• Solubility.: Chloroform, Ethyl Acetate, Methanol
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 452.01300
• Heavy Atom Count: 22
• Complexity: 553

Purity/Quality:

97% ^*data from raw suppliers

2,3,3a,6,7,7a-Hexahydro-2S,7a-dimethyl-4-hydroxy-indene-1R-(1’-iodo)ethane4-O-Trifluoromethylsulfonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CI)C1CCC2C1(CCC=C2OS(=O)(=O)C(F)(F)F)C
• Isomeric SMILES: C[C@H](CI)[C@H]1CC[C@@H]2[C@@]1(CCC=C2OS(=O)(=O)C(F)(F)F)C
• Uses: Intermediate in the preparation of Dihydroxyvitamin D3 and associated metabolites.

Technology Process of [(1R,3aR,7aR)-1-[(2S)-1-iodopropan-2-yl]-7a-methyl-1,2,3,3a,6,7-hexahydroinden-4-yl] trifluoromethanesulfonate

There total 3 articles about [(1R,3aR,7aR)-1-[(2S)-1-iodopropan-2-yl]-7a-methyl-1,2,3,3a,6,7-hexahydroinden-4-yl] trifluoromethanesulfonate 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: 92.0%

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + des-A,B-22-iodo-23,24-dinorcholan-8-one (145372-32-3) → des-A,B-22-iodo-23,24-dinorchol-8-enyl trifluoromethanesulfonate (145372-33-4)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 2h;

DOI:10.1021/jo00053a023

Reference yield:

(8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol (64190-52-9) → des-A,B-22-iodo-23,24-dinorchol-8-enyl trifluoromethanesulfonate (145372-33-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / Ph₃P, imidazole, I₂ / tetrahydrofuran / -20 deg C, 15 min then RT, 1.5 h

2: 90 percent / PDC / CH₂Cl₂ / 6 h / Ambient temperature

3: 92 percent / LDA / tetrahydrofuran / 2 h / -78 °C

With 1H-imidazole; dipyridinium dichromate; iodine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00053a023

Reference yield:

(1R,3aR,4S,7aR)-octahydro-1-[(S)-1-iodopropan-2-yl]-7a-methyl-1H-inden-4-ol (116535-65-0) → des-A,B-22-iodo-23,24-dinorchol-8-enyl trifluoromethanesulfonate (145372-33-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / PDC / CH₂Cl₂ / 6 h / Ambient temperature

2: 92 percent / LDA / tetrahydrofuran / 2 h / -78 °C

With dipyridinium dichromate; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00053a023

upstream raw materials:

N,N-phenylbistrifluoromethane-sulfonimide

des-A,B-22-iodo-23,24-dinorcholan-8-one

(8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol

(1R,3aR,4S,7aR)-octahydro-1-[(S)-1-iodopropan-2-yl]-7a-methyl-1H-inden-4-ol

Downstream raw materials:

1α-[(tert-butyldimethylsilyl)oxy]-24-(methoxycarbonyl)-25,26,27-trisnorvitamin D3 tert-butyldimethylsilyl ether

1α-<(tert-butyldimethylsilyl)-oxy>-6,7-didehydro-24-(methoxycarbonyl)-25,26,27-trisnorprevitamin D₃ tert-butyldimethylsilyl ether