[(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 2-[3-(tert-butyldimethylsilyloxy)phenyl]ethyl ester

Base Information

• Chemical Name: [(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 2-[3-(tert-butyldimethylsilyloxy)phenyl]ethyl ester
• CAS No.: 951377-89-2
• Molecular Formula: C₂₆H₄₀O₅Si
• Molecular Weight: 460.686

Synonyms:[(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 2-[3-(tert-butyldimethylsilyloxy)phenyl]ethyl ester

Chemical Property of [(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 2-[3-(tert-butyldimethylsilyloxy)phenyl]ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 2-[3-(tert-butyldimethylsilyloxy)phenyl]ethyl ester

There total 8 articles about [(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 2-[3-(tert-butyldimethylsilyloxy)phenyl]ethyl ester 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: 82.0%

[(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid (869476-95-9) + tert-butyldimethylsilyl 3-(2-hydroxyethyl)phenyl ether (160701-58-6) → [(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 2-[3-(tert-butyldimethylsilyloxy)phenyl]ethyl ester (951377-89-2)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 23 ℃;

DOI:10.1021/jo071146k

Reference yield:

(3aR,6aR)-2,2-Dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one (115509-13-2) → [(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 2-[3-(tert-butyldimethylsilyloxy)phenyl]ethyl ester (951377-89-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / hydrogen / Pd/C / ethyl acetate / 20 °C

2: 57 percent / LHMDS; HMPA; Me₂Zn / tetrahydrofuran; toluene / -78 - -45 °C

3: KHMDS; CeCl₃ / tetrahydrofuran / -45 °C

4: 100 percent / LiOH / tetrahydrofuran; methanol; H₂O / 1 h / 20 °C

5: 82 percent / N,N'-dicyclohexylcarbodiimide; 4-dimethylaminopyridine / CH₂Cl₂ / 0 - 23 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium hydroxide; cerium(III) chloride; hydrogen; dimethyl zinc(II); potassium hexamethylsilazane; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; toluene; 3: Wittig reaction;

DOI:10.1021/jo071146k

Reference yield:

((3aS,4R,6aS)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol (129263-68-9,828937-29-7) → [(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 2-[3-(tert-butyldimethylsilyloxy)phenyl]ethyl ester (951377-89-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: pyridinium chlorochromate / benzene / 10.5 h / Heating

1.2: 1.16 g / pyridinium chlorochromate / benzene / 14.5 h / Heating

2.1: 85 percent / n-butyllithium / tetrahydrofuran; hexane / 3 h / -78 - 23 °C

3.1: 95 percent / hydrogen / Pd/C / ethyl acetate / 20 °C

4.1: 57 percent / LHMDS; HMPA; Me₂Zn / tetrahydrofuran; toluene / -78 - -45 °C

5.1: KHMDS; CeCl₃ / tetrahydrofuran / -45 °C

6.1: 100 percent / LiOH / tetrahydrofuran; methanol; H₂O / 1 h / 20 °C

7.1: 82 percent / N,N'-dicyclohexylcarbodiimide; 4-dimethylaminopyridine / CH₂Cl₂ / 0 - 23 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium hydroxide; n-butyllithium; cerium(III) chloride; hydrogen; dimethyl zinc(II); potassium hexamethylsilazane; dicyclohexyl-carbodiimide; pyridinium chlorochromate; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; toluene; benzene; 5.1: Wittig reaction;

DOI:10.1021/jo071146k

upstream raw materials:

[(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid

tert-butyldimethylsilyl 3-(2-hydroxyethyl)phenyl ether

((3aR,5S,6aR)-2,2-dimethyl-4-oxotetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl)acetic acid methyl ester

[(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid methyl ester

Downstream raw materials:

C₉H₁₄O₄C₈H₈O

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