1-[1-(tert-butyldimethylsiloxy)ethyl]-1-methoxycarbonyl-2-cyclohexen-4-one

Base Information

• Chemical Name: 1-[1-(tert-butyldimethylsiloxy)ethyl]-1-methoxycarbonyl-2-cyclohexen-4-one
• CAS No.: 224035-85-2
• Molecular Formula: C₁₆H₂₈O₄Si
• Molecular Weight: 312.481
• Mol file: 224035-85-2.mol

Synonyms:1-[1-(tert-butyldimethylsiloxy)ethyl]-1-methoxycarbonyl-2-cyclohexen-4-one

Chemical Property of 1-[1-(tert-butyldimethylsiloxy)ethyl]-1-methoxycarbonyl-2-cyclohexen-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[1-(tert-butyldimethylsiloxy)ethyl]-1-methoxycarbonyl-2-cyclohexen-4-one

There total 1 articles about 1-[1-(tert-butyldimethylsiloxy)ethyl]-1-methoxycarbonyl-2-cyclohexen-4-one 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: 96.0%

danishefsky's diene (54125-02-9) + (+/-)-2-[1-(tert-butyldimethylsilanyloxy)ethyl]acrylic acid methyl ester (118558-96-6) → 1-[1-(tert-butyldimethylsiloxy)ethyl]-1-methoxycarbonyl-2-cyclohexen-4-one (224035-85-2)

Guidance literature:

In 1,2-dichloro-benzene; at 180 ℃;

DOI:10.1016/S0040-4039(99)00047-7

Reference yield:

1-[1-(tert-butyldimethylsiloxy)ethyl]-1-methoxycarbonyl-2-cyclohexen-4-one (224035-85-2) → 1-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-cyclohexanecarboxylic acid methyl ester

Guidance literature:

With hydrogen; palladium on activated charcoal;

DOI:10.1016/S0040-4039(99)00047-7

Reference yield:

1-[1-(tert-butyldimethylsiloxy)ethyl]-1-methoxycarbonyl-2-cyclohexen-4-one (224035-85-2) → (-)-(1R,2R)-1-benzoyloxy-2-{8-(methoxymethoxy)methyl-1,4-dioxaspiro[4,5]dec-8-yl}-2-methylcyclobutane

Guidance literature:

Multi-step reaction with 12 steps

1: H₂ / Pd/C / methanol / 13 h / 20 °C

2: 31.0 g / PPTS / benzene / 5 h / Heating

3: DIBALH / CH₂Cl₂ / 1.5 h / -78 °C

4: 26.0 g / DIPEA / CH₂Cl₂ / 12 h / 0 - 20 °C

5: 97 percent / TBAF / tetrahydrofuran / 20 h / 50 °C

6: 93 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.83 h / -78 - 0 °C

7: 72 percent / NaH / 1,2-dimethoxy-ethane / 12 h / 95 °C

8: 85 percent / OsO₄; DABCO; K₃Fe(CN)6/K₂CO₃ / 2-methyl-propan-2-ol; H₂O / 20 h / 20 °C

9: SO₂Cl₂; imidazole / CH₂Cl₂ / 0.33 h / 0 °C

10: Florisil / CH₂Cl₂ / 18 h / -78 - 20 °C

11: 87 percent / NaBH₄ / methanol / 3 h

12: 95 percent / DMAP; Et₃N / CH₂Cl₂ / 33 h / Heating

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; dmap; sodium tetrahydroborate; florisil; osmium(VIII) oxide; sulfuryl dichloride; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; potassium hexacyanoferrate(III); palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water; tert-butyl alcohol; benzene; 1: Hydrogenation / 2: Cyclization / 3: Reduction / 4: Etherification / 5: Substitution / 6: Oxidation / 7: Wittig reaction / 8: dihydroxylation / 9: Condensation / 10: Elimination / 11: Reduction / 12: Acylation;

DOI:10.1021/jo991430e

upstream raw materials:

danishefsky's diene

(+/-)-2-[1-(tert-butyldimethylsilanyloxy)ethyl]acrylic acid methyl ester

Downstream raw materials:

4-(3-hydroxy-1-methyl-2-methylene-cyclopentyl)-4-methoxymethoxymethyl-cyclohex-2-enone

(+/-)-4-deoxyverrucarol

(+/-)-1-(3-hydroxy-1-methyl-2-methylenecyclopentyl)-1-(methoxymethoxy)methyl-4-cyclohexanone