(3S,4S,S_R)-3-(tert-butyldimethylsilyloxy)-4-[2-(N,N-dimethylamino)phenylsulfinyl]-2-(triisopropylsilyloxy)methylcyclopentene

Base Information

• Chemical Name: (3S,4S,S_R)-3-(tert-butyldimethylsilyloxy)-4-[2-(N,N-dimethylamino)phenylsulfinyl]-2-(triisopropylsilyloxy)methylcyclopentene
• CAS No.: 816425-56-6
• Molecular Formula: C₂₉H₅₃NO₃SSi₂
• Molecular Weight: 551.982

Synonyms:(3S,4S,S_R)-3-(tert-butyldimethylsilyloxy)-4-[2-(N,N-dimethylamino)phenylsulfinyl]-2-(triisopropylsilyloxy)methylcyclopentene

Chemical Property of (3S,4S,S_R)-3-(tert-butyldimethylsilyloxy)-4-[2-(N,N-dimethylamino)phenylsulfinyl]-2-(triisopropylsilyloxy)methylcyclopentene

Chemical Property:

Purity/Quality:

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Technology Process of (3S,4S,S_R)-3-(tert-butyldimethylsilyloxy)-4-[2-(N,N-dimethylamino)phenylsulfinyl]-2-(triisopropylsilyloxy)methylcyclopentene

There total 8 articles about (3S,4S,S_R)-3-(tert-butyldimethylsilyloxy)-4-[2-(N,N-dimethylamino)phenylsulfinyl]-2-(triisopropylsilyloxy)methylcyclopentene 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: 99.0%

(1S,5S,SR)-5-[2-(N,N-dimethylamino)phenylsulfinyl]-2-(triisopropylsilyloxy)methyl-2-cyclopenten-1-ol (816425-54-4) + tert-butyldimethylsilyl chloride (18162-48-6) → (3S,4S,SR)-3-(tert-butyldimethylsilyloxy)-4-[2-(N,N-dimethylamino)phenylsulfinyl]-2-(triisopropylsilyloxy)methylcyclopentene (816425-56-6)

Guidance literature:

With 1H-imidazole; In acetonitrile; at 20 ℃; for 14h;

DOI:10.1002/chem.200400443

Reference yield:

N,N-dimethyl-o-iodoaniline (698-02-2) → (3S,4S,SR)-3-(tert-butyldimethylsilyloxy)-4-[2-(N,N-dimethylamino)phenylsulfinyl]-2-(triisopropylsilyloxy)methylcyclopentene (816425-56-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: n-BuLi / hexane; diethyl ether / 1 h / -78 °C

1.2: 61 percent / hexane; diethyl ether; tetrahydrofuran / -78 °C

2.1: tetrahydrofuran / -78 °C

3.2: N-methylmorpholine N-oxide*H₂O / acetonitrile

4.1: 96 percent / DIBALH / tetrahydrofuran / 1 h / -78 °C

5.1: 99 percent / imidazole / acetonitrile / 14 h / 20 °C

With 1H-imidazole; n-butyllithium; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; hexane; acetonitrile; 3.2: intermolecular Pauson-Khand reaction;

DOI:10.1002/chem.200400443

Reference yield:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → (3S,4S,SR)-3-(tert-butyldimethylsilyloxy)-4-[2-(N,N-dimethylamino)phenylsulfinyl]-2-(triisopropylsilyloxy)methylcyclopentene (816425-56-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 24 h / 20 °C

2.2: N-methylmorpholine N-oxide*H₂O / acetonitrile

3.1: 96 percent / DIBALH / tetrahydrofuran / 1 h / -78 °C

4.1: 99 percent / imidazole / acetonitrile / 14 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; acetonitrile; 2.2: intermolecular Pauson-Khand reaction;

DOI:10.1002/chem.200400443

upstream raw materials:

(1S,5S,S_R)-5-[2-(N,N-dimethylamino)phenylsulfinyl]-2-(triisopropylsilyloxy)methyl-2-cyclopenten-1-ol

tert-butyldimethylsilyl chloride

N,N-dimethyl-o-iodoaniline

triisopropylsilyl trifluoromethanesulfonate

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