(1'S^*,3R^*,4S^*)-3-<1-(dimethylphenylsilyl)ethyl>-4-methoxycarbonyl-1-(4-methoxyphenyl)azetidin-2-one

Base Information

• Chemical Name: (1'S^*,3R^*,4S^*)-3-<1-(dimethylphenylsilyl)ethyl>-4-methoxycarbonyl-1-(4-methoxyphenyl)azetidin-2-one
• CAS No.: 128571-96-0
• Molecular Formula: C₂₂H₂₇NO₄Si
• Molecular Weight: 397.546

Synonyms:(1'S^*,3R^*,4S^*)-3-<1-(dimethylphenylsilyl)ethyl>-4-methoxycarbonyl-1-(4-methoxyphenyl)azetidin-2-one

Chemical Property of (1'S^*,3R^*,4S^*)-3-<1-(dimethylphenylsilyl)ethyl>-4-methoxycarbonyl-1-(4-methoxyphenyl)azetidin-2-one

Chemical Property:

Purity/Quality:

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Technology Process of (1'S^*,3R^*,4S^*)-3-<1-(dimethylphenylsilyl)ethyl>-4-methoxycarbonyl-1-(4-methoxyphenyl)azetidin-2-one

There total 6 articles about (1'S^*,3R^*,4S^*)-3-<1-(dimethylphenylsilyl)ethyl>-4-methoxycarbonyl-1-(4-methoxyphenyl)azetidin-2-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:

dimethyl(phenyl)silyllithium (3839-31-4) + E-3-Ethylidene-4-(methoxycarbonyl)-1-(4-methoxyphenyl)azetidin-2-one (131533-35-2) → (2S,3S)-3-[(S)-1-(Dimethyl-phenyl-silanyl)-ethyl]-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carboxylic acid methyl ester (128571-95-9) + (2R,3S)-3-[(S)-1-(Dimethyl-phenyl-silanyl)-ethyl]-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carboxylic acid methyl ester (128474-84-0,128571-95-9,128571-96-0,128571-97-1)

Guidance literature:

With CuCN; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1021/jo00014a017

Reference yield:

dimethyl(phenyl)silyllithium (3839-31-4) + Z-3-Ethylidene-4-(methoxycarbonyl)-1-(4-methoxyphenyl)azetidin-2-one (124156-30-5,124156-31-6,131533-34-1,131533-35-2) → (2S,3S)-3-[(S)-1-(Dimethyl-phenyl-silanyl)-ethyl]-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carboxylic acid methyl ester (128571-95-9) + (2R,3S)-3-[(S)-1-(Dimethyl-phenyl-silanyl)-ethyl]-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carboxylic acid methyl ester (128474-84-0,128571-95-9,128571-96-0,128571-97-1)

Guidance literature:

With CuCN; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1021/jo00014a017

Reference yield:

(4-methoxyphenyl-benzylidene)-carbamic acid methyl ester (124156-20-3,72079-55-1) → (2R,3S)-3-[(S)-1-(Dimethyl-phenyl-silanyl)-ethyl]-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carboxylic acid methyl ester (128474-84-0,128571-95-9,128571-96-0,128571-97-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) NEt₃, 2) m-chloroperbenzoic acid / 1) CH₂Cl₂, r.t., overnight; 2) CH₂Cl₂, 1 h, 0 deg C

2: 160 °C / 0.1 - 0.2 Torr

3: CuCN / tetrahydrofuran / 0.5 h / 0 °C

With triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran;

DOI:10.1021/jo00014a017

upstream raw materials:

crotonic acid methyl ester

dimethyl(phenyl)silyllithium

(4-methoxyphenyl-benzylidene)-carbamic acid methyl ester

E-3-Ethylidene-4-(methoxycarbonyl)-1-(4-methoxyphenyl)azetidin-2-one

Downstream raw materials:

Z-3-Ethylidene-4-(methoxycarbonyl)-1-(4-methoxyphenyl)azetidin-2-one

E-3-Ethylidene-4-(methoxycarbonyl)-1-(4-methoxyphenyl)azetidin-2-one

trans-1-p-anisyl-3-acetyl-4-carbomethoxy-2-azetidinone

(1'S^*,3R^*,4S^*)-3-(1-hydroxyethyl)-4-methoxycarbonyl-1-(4-methoxyphenyl)azetidin-2-one

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