methyl (2E,7R)-2-(t-butyldimethylsilyloxy)methyl-7-(t-butyldiphenylsilyloxy)-2-octenoate

Base Information

• Chemical Name: methyl (2E,7R)-2-(t-butyldimethylsilyloxy)methyl-7-(t-butyldiphenylsilyloxy)-2-octenoate
• CAS No.: 854612-94-5
• Molecular Formula: C₃₂H₅₀O₄Si₂
• Molecular Weight: 554.918

Synonyms:methyl (2E,7R)-2-(t-butyldimethylsilyloxy)methyl-7-(t-butyldiphenylsilyloxy)-2-octenoate

Chemical Property of methyl (2E,7R)-2-(t-butyldimethylsilyloxy)methyl-7-(t-butyldiphenylsilyloxy)-2-octenoate

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of methyl (2E,7R)-2-(t-butyldimethylsilyloxy)methyl-7-(t-butyldiphenylsilyloxy)-2-octenoate

There total 12 articles about methyl (2E,7R)-2-(t-butyldimethylsilyloxy)methyl-7-(t-butyldiphenylsilyloxy)-2-octenoate 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: 93.0%

methyl (2E,7R)-7-(t-butyldiphenylsilyloxy)-2-hydroxymethyl-2-octenoate (854612-93-4) + tert-butyldimethylsilyl chloride (18162-48-6) → methyl (2E,7R)-2-(t-butyldimethylsilyloxy)methyl-7-(t-butyldiphenylsilyloxy)-2-octenoate (854612-94-5)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃; for 1h;

DOI:10.1021/ol050763x

Reference yield:

(R)-2-(tert-butyldiphenylsilanyloxy)propionic acid methyl ester (561038-05-9) → methyl (2E,7R)-2-(t-butyldimethylsilyloxy)methyl-7-(t-butyldiphenylsilyloxy)-2-octenoate (854612-94-5)

Guidance literature:

Multi-step reaction with 11 steps

1.1: DIBAL-H / toluene / 1.5 h / -78 °C

2.1: 30.0 g / LiCl; DBU / acetonitrile / 1 h

3.1: H₂ / Pd/C / ethanol / 23 h

4.1: 21.0 g / DIBAL-H / CH₂Cl₂; toluene / 2 h / -18 °C

5.1: 100 percent / PPh₃; I₂; imidazole / acetonitrile; tetrahydrofuran / 1 h / 0 °C

6.1: 95 percent / dimethylsulfoxide / 5.5 h / 0 °C

7.1: DIBAL-H / toluene / 2 h / -78 °C

7.2: 95 percent / HCl; NH₄Cl / H₂O / -78 - 20 °C

8.1: 86 percent / DABCO / methanol / 120 h

9.1: 95 percent / NBS; Me₂S / CH₂Cl₂ / 6 h / 0 °C

10.1: 81 percent / Na₂HPO₄; NaH₂PO₄ / CH₂Cl₂; various solvent(s) / 7 h / 100 °C

11.1: 93 percent / imidazole / dimethylformamide / 1 h / 0 °C

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; disodium hydrogenphosphate; sodium dihydrogenphosphate; N-Bromosuccinimide; dimethylsulfide; hydrogen; iodine; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; 2.1: Horner-Emmons olefination / 8.1: Morita-Baylis-Hillman reaction;

DOI:10.1021/ol050763x

Reference yield:

ethyl (2E,4R)-4-(t-butyldiphenylsilyloxy)-2-pentenoate (854612-89-8) → methyl (2E,7R)-2-(t-butyldimethylsilyloxy)methyl-7-(t-butyldiphenylsilyloxy)-2-octenoate (854612-94-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: H₂ / Pd/C / ethanol / 23 h

2.1: 21.0 g / DIBAL-H / CH₂Cl₂; toluene / 2 h / -18 °C

3.1: 100 percent / PPh₃; I₂; imidazole / acetonitrile; tetrahydrofuran / 1 h / 0 °C

4.1: 95 percent / dimethylsulfoxide / 5.5 h / 0 °C

5.1: DIBAL-H / toluene / 2 h / -78 °C

5.2: 95 percent / HCl; NH₄Cl / H₂O / -78 - 20 °C

6.1: 86 percent / DABCO / methanol / 120 h

7.1: 95 percent / NBS; Me₂S / CH₂Cl₂ / 6 h / 0 °C

8.1: 81 percent / Na₂HPO₄; NaH₂PO₄ / CH₂Cl₂; various solvent(s) / 7 h / 100 °C

9.1: 93 percent / imidazole / dimethylformamide / 1 h / 0 °C

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; disodium hydrogenphosphate; sodium dihydrogenphosphate; N-Bromosuccinimide; dimethylsulfide; hydrogen; iodine; diisobutylaluminium hydride; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; 6.1: Morita-Baylis-Hillman reaction;

DOI:10.1021/ol050763x

upstream raw materials:

methyl (2E,7R)-7-(t-butyldiphenylsilyloxy)-2-hydroxymethyl-2-octenoate

tert-butyldimethylsilyl chloride

(R)-2-(tert-butyldiphenylsilanyloxy)propionic acid methyl ester

(5R)-5-[1-(tert-butyl)-1,1-diphenylsilyl]oxyhexanal

Downstream raw materials:

(4R)-4-benzyl-3-[(2R,3R,4E,9R)-4-(t-butyldimethylsilyloxy)methyl-9-(t-butyldiphenylsilyloxy)-3-methoxymethoxy-2-methyldec-4-enoyl]oxazolidin-2-one

(3S,4R,5E,10R)-1,1-dibromo-5-(t-butyldimethylsilyloxy)methyl-10-(t-butyldiphenylsilyloxy)-4-methoxymethoxy-3-methylundeca-1,5-diene

(2S,3R,4E,9R)-4-(t-butyldimethylsilyloxy)methyl-9-(t-butyldiphenylsilyloxy)-3-methoxymethoxy-2-methyldec-4-en-1-ol

(2S,3R,4E,9R)-4-(t-butyldimethylsilyloxy)methyl-9-(t-butyldiphenylsilyloxy)-3-methoxymethoxy-2-methyldec-4-enal

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