[(2R,3S)-2-(1,1-Dimethyl-2-phenylsulfanyl-ethyl)-3-methoxy-4-oxo-azetidin-1-yl]-acetic acid ethyl ester

Base Information

• Chemical Name: [(2R,3S)-2-(1,1-Dimethyl-2-phenylsulfanyl-ethyl)-3-methoxy-4-oxo-azetidin-1-yl]-acetic acid ethyl ester
• CAS No.: 86255-86-9
• Molecular Formula: C₁₈H₂₅NO₄S
• Molecular Weight: 351.467

Synonyms:[(2R,3S)-2-(1,1-Dimethyl-2-phenylsulfanyl-ethyl)-3-methoxy-4-oxo-azetidin-1-yl]-acetic acid ethyl ester

Chemical Property of [(2R,3S)-2-(1,1-Dimethyl-2-phenylsulfanyl-ethyl)-3-methoxy-4-oxo-azetidin-1-yl]-acetic acid ethyl ester

Chemical Property:

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Technology Process of [(2R,3S)-2-(1,1-Dimethyl-2-phenylsulfanyl-ethyl)-3-methoxy-4-oxo-azetidin-1-yl]-acetic acid ethyl ester

There total 2 articles about [(2R,3S)-2-(1,1-Dimethyl-2-phenylsulfanyl-ethyl)-3-methoxy-4-oxo-azetidin-1-yl]-acetic acid 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: 81.0%

Methoxyacetyl chloride (38870-89-2) + [2,2-Dimethyl-3-phenylsulfanyl-prop-(Z)-ylideneamino]-acetic acid ethyl ester (86255-85-8) → [(2R,3S)-2-(1,1-Dimethyl-2-phenylsulfanyl-ethyl)-3-methoxy-4-oxo-azetidin-1-yl]-acetic acid ethyl ester (86255-86-9)

Guidance literature:

With triethylamine; In dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4039(00)81349-0

Reference yield:

3-(phenylthio)-2,2-dimethylpropanal (20967-51-5) → [(2R,3S)-2-(1,1-Dimethyl-2-phenylsulfanyl-ethyl)-3-methoxy-4-oxo-azetidin-1-yl]-acetic acid ethyl ester (86255-86-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / triethylamine, magnesium sulfate / CH₂Cl₂

2: 81 percent / triethylamine / CH₂Cl₂ / Ambient temperature

With magnesium sulfate; triethylamine; In dichloromethane;

DOI:10.1016/S0040-4039(00)81349-0

Reference yield: 98.0%

[(2R,3S)-2-(1,1-Dimethyl-2-phenylsulfanyl-ethyl)-3-methoxy-4-oxo-azetidin-1-yl]-acetic acid ethyl ester (86255-86-9) → [(2S,3R)-2-(1,1-Dimethyl-2-phenylsulfanyl-ethyl)-3-methoxy-4-oxo-azetidin-1-yl]-acetic acid (86255-87-0)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; Ambient temperature;

DOI:10.1016/S0040-4039(00)81349-0

upstream raw materials:

Methoxyacetyl chloride

[2,2-Dimethyl-3-phenylsulfanyl-prop-(Z)-ylideneamino]-acetic acid ethyl ester

3-(phenylthio)-2,2-dimethylpropanal

Downstream raw materials:

[(2S,3R)-2-(1,1-Dimethyl-2-phenylsulfanyl-ethyl)-3-methoxy-4-oxo-azetidin-1-yl]-acetic acid

[(2R,3S)-2-(1,1-Dimethyl-2-phenylsulfanyl-ethyl)-3-methoxy-4-oxo-azetidin-1-yl]-acetic acid 2-trimethylsilanyl-ethyl ester

[(2R,3S)-2-(2-Chloro-1,1-dimethyl-2-phenylsulfanyl-ethyl)-3-methoxy-4-oxo-azetidin-1-yl]-acetic acid 2-trimethylsilanyl-ethyl ester

[(2R,3S)-2-(1,1-Dimethyl-2,2-bis-phenylsulfanyl-ethyl)-3-methoxy-4-oxo-azetidin-1-yl]-acetic acid 2-trimethylsilanyl-ethyl ester

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