(1'S,4'S,5'S)-2-<4'-<3-(tert-Butyldimethylsilyloxy)-2,2-dimethylpropyl>-5'-(4-methoxybenzyloxy)-2'-methylcyclopent-2'-enyl>essigsaeure

Base Information

• Chemical Name: (1'S,4'S,5'S)-2-<4'-<3-(tert-Butyldimethylsilyloxy)-2,2-dimethylpropyl>-5'-(4-methoxybenzyloxy)-2'-methylcyclopent-2'-enyl>essigsaeure
• CAS No.: 154952-66-6
• Molecular Formula: C₂₇H₄₄O₅Si
• Molecular Weight: 476.729

Synonyms:(1'S,4'S,5'S)-2-<4'-<3-(tert-Butyldimethylsilyloxy)-2,2-dimethylpropyl>-5'-(4-methoxybenzyloxy)-2'-methylcyclopent-2'-enyl>essigsaeure

Chemical Property of (1'S,4'S,5'S)-2-<4'-<3-(tert-Butyldimethylsilyloxy)-2,2-dimethylpropyl>-5'-(4-methoxybenzyloxy)-2'-methylcyclopent-2'-enyl>essigsaeure

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of (1'S,4'S,5'S)-2-<4'-<3-(tert-Butyldimethylsilyloxy)-2,2-dimethylpropyl>-5'-(4-methoxybenzyloxy)-2'-methylcyclopent-2'-enyl>essigsaeure

There total 1 articles about (1'S,4'S,5'S)-2-<4'-<3-(tert-Butyldimethylsilyloxy)-2,2-dimethylpropyl>-5'-(4-methoxybenzyloxy)-2'-methylcyclopent-2'-enyl>essigsaeure 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:

1-bromo-3-<(tert-butyldimethylsilyl)oxy>-2,2-dimethylpropane (111849-25-3) + (3aR,4S,6aS)-(+)-4-(4-Methoxybenzyloxy)-6a-methyl-3,3a,4,6a-tetrahydro-2H-cyclopentafuran-2-on (154952-65-5) → (1'S,4'S,5'S)-2-<4'-<3-(tert-Butyldimethylsilyloxy)-2,2-dimethylpropyl>-5'-(4-methoxybenzyloxy)-2'-methylcyclopent-2'-enyl>essigsaeure (154952-66-6)

Guidance literature:

With dimethylsulfide; lithium-sodium alloy; copper(I) bromide; Multistep reaction; 1.) ether, 1 h, RT; 2.) THF; 1 h, -78 deg C; 45 min;

Reference yield: 87.0%

(1'S,4'S,5'S)-2-<4'-<3-(tert-Butyldimethylsilyloxy)-2,2-dimethylpropyl>-5'-(4-methoxybenzyloxy)-2'-methylcyclopent-2'-enyl>essigsaeure (154952-66-6) → (1'S,4'S,5'S)-(+)-2-<4'-<3-(tert-Butyldimethylsilyloxy)-2,2-dimethylpropyl>-5'-(4-methoxybenzyloxy)-2'-methylcyclopent-2'-enyl>ethanol (154952-67-7)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 1h; Ambient temperature;

Reference yield:

(1'S,4'S,5'S)-2-<4'-<3-(tert-Butyldimethylsilyloxy)-2,2-dimethylpropyl>-5'-(4-methoxybenzyloxy)-2'-methylcyclopent-2'-enyl>essigsaeure (154952-66-6) → (3aR,3bR,4R,6aS,7S,7aS)-(+)-Decahydro-4-hydroxy-7-(4-methoxybenzyloxy)-3a,5,5-trimethyl-3-methylen-2H-cyclopentapentalen-2-on (154952-75-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 87 percent / LiAlH₄ / tetrahydrofuran / 1 h / Ambient temperature

2: 78 percent / AcONa, molecular sieve (3 Angstroem), Al₂O₃, pyridinium chlorochromate / CH₂Cl₂ / 3 h

3: 1.) 1.6M BuLi / 1.) THF, hexane, 0 deg C, 10 min; 2.) 0 deg C, 30 min

4: AcONa, molecular sieve (3 Angstroem), Al₂O₃, pyridinium chlorochromate / CH₂Cl₂ / 6 h

5: trimethylorthoformate, p-toluenesulfonic acid monohydrate / benzene / 1.) 6 h, RT; 2.) 6 h, reflux

6: Bu₄NF*3H₂O / tetrahydrofuran / 12 h / Ambient temperature

7: 79 percent / AcONa, molecular sieve (3 Angstroem), Al₂O₃, pyridinium chlorochromate / CH₂Cl₂ / 2 h / Ambient temperature

8: SmI₂, HMPT, tBuOH / tetrahydrofuran / 0.17 h / 0 °C

9: p-toluenesulfonic acid monohydrate / acetone / 12 h / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; aluminum oxide; lithium aluminium tetrahydride; n-butyllithium; samarium diiodide; 3 A molecular sieve; tetrabutyl ammonium fluoride; sodium acetate; toluene-4-sulfonic acid; pyridinium chlorochromate; tert-butyl alcohol; trimethyl orthoformate; In tetrahydrofuran; dichloromethane; acetone; benzene;

upstream raw materials:

1-bromo-3-<(tert-butyldimethylsilyl)oxy>-2,2-dimethylpropane

(3aR,4S,6aS)-(+)-4-(4-Methoxybenzyloxy)-6a-methyl-3,3a,4,6a-tetrahydro-2H-cyclopentafuran-2-on

Downstream raw materials:

(1'S,4'S,5'S)-(+)-2-<4'-<3-(tert-Butyldimethylsilyloxy)-2,2-dimethylpropyl>-5'-(4-methoxybenzyloxy)-2'-methylcyclopent-2'-enyl>ethanol

(-)-Coriolin

(3aR,3bR,4R,6aS,7S,7aS)-(+)-Decahydro-4-hydroxy-7-(4-methoxybenzyloxy)-3a,5,5-trimethyl-3-methylen-2H-cyclopentapentalen-2-on

(1'S,4'S,5'S)-2-<4'-<3-(tert-Butyldimethylsilyloxy)-2,2-dimethylpropyl>-5'-(4-methoxybenzyloxy)-2'-methylcyclopent-2'-enyl>acetaldehyd

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