2-[(1S,2R)-1-(4-Methoxycarbonyl-phenyl)-2-methyl-4-trimethylsilanyl-but-3-ynyl]-malonic acid diethyl ester

Base Information

• Chemical Name: 2-[(1S,2R)-1-(4-Methoxycarbonyl-phenyl)-2-methyl-4-trimethylsilanyl-but-3-ynyl]-malonic acid diethyl ester
• CAS No.: 378251-01-5
• Molecular Formula: C₂₃H₃₂O₆Si
• Molecular Weight: 432.589

Synonyms:2-[(1S,2R)-1-(4-Methoxycarbonyl-phenyl)-2-methyl-4-trimethylsilanyl-but-3-ynyl]-malonic acid diethyl ester

Chemical Property of 2-[(1S,2R)-1-(4-Methoxycarbonyl-phenyl)-2-methyl-4-trimethylsilanyl-but-3-ynyl]-malonic acid diethyl ester

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Technology Process of 2-[(1S,2R)-1-(4-Methoxycarbonyl-phenyl)-2-methyl-4-trimethylsilanyl-but-3-ynyl]-malonic acid diethyl ester

There total 1 articles about 2-[(1S,2R)-1-(4-Methoxycarbonyl-phenyl)-2-methyl-4-trimethylsilanyl-but-3-ynyl]-malonic acid diethyl 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:

diethyl (S)-1-methyl-3-trimethylsilylprop-2-ynyl phosphate + 1,3-diethyl 2-{[4-(methoxycarbonyl)phenyl]methylidene}propanedioate → 2-[(1S,2R)-1-(4-Methoxycarbonyl-phenyl)-2-methyl-4-trimethylsilanyl-but-3-ynyl]-malonic acid diethyl ester (378251-01-5)

Guidance literature:

diethyl (S)-1-methyl-3-trimethylsilylprop-2-ynyl phosphate; With titanium(IV) isopropylate; isopropylmagnesium chloride; In diethyl ether; at -50 - -40 ℃;

2-(4-methoxycarbonyl-benzylidene)-malonic acid diethyl ester; In diethyl ether; at -40 - -20 ℃; for 1h; Further stages.;

DOI:10.1021/ol016652p

Reference yield: 87.0%

2-[(1S,2R)-1-(4-Methoxycarbonyl-phenyl)-2-methyl-4-trimethylsilanyl-but-3-ynyl]-malonic acid diethyl ester (378251-01-5) → 4-((1R,2R)-1-Carboxymethyl-2-methyl-but-3-ynyl)-benzoic acid

Guidance literature:

2-[(1S,2R)-1-(4-Methoxycarbonyl-phenyl)-2-methyl-4-trimethylsilanyl-but-3-ynyl]-malonic acid diethyl ester; With potassium hydroxide; In methanol; at 20 ℃;

With hydrogenchloride; In methanol;

In ethanol; for 4h; Further stages.; Heating;

DOI:10.1021/ol016652p

Reference yield:

2-[(1S,2R)-1-(4-Methoxycarbonyl-phenyl)-2-methyl-4-trimethylsilanyl-but-3-ynyl]-malonic acid diethyl ester (378251-01-5) → 4-{(1R,2R)-2-Methyl-1-[((S)-1-phenyl-ethylcarbamoyl)-methyl]-but-3-ynyl}-N-((S)-1-phenyl-ethyl)-benzamide

Guidance literature:

Multi-step reaction with 2 steps

1.1: aq.KOH / methanol / 20 °C

1.2: aq.HCl / methanol

1.3: 87 percent / ethanol / 4 h / Heating

2.1: 70 percent / (i-Pr)2NEt; PyBOP / dimethylformamide / 2 h / 20 °C

With potassium hydroxide; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/ol016652p

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