tert-butyl (-)-(1S,2S,R_S)-1-dimethylphosphono-2-(p-tolylsulfinyl)cyclopropane-1-carboxylate

Base Information

• Chemical Name: tert-butyl (-)-(1S,2S,R_S)-1-dimethylphosphono-2-(p-tolylsulfinyl)cyclopropane-1-carboxylate
• CAS No.: 1422157-39-8
• Molecular Formula: C₁₇H₂₅O₆PS
• Molecular Weight: 388.422

Synonyms:tert-butyl (-)-(1S,2S,R_S)-1-dimethylphosphono-2-(p-tolylsulfinyl)cyclopropane-1-carboxylate

Chemical Property of tert-butyl (-)-(1S,2S,R_S)-1-dimethylphosphono-2-(p-tolylsulfinyl)cyclopropane-1-carboxylate

Chemical Property:

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Technology Process of tert-butyl (-)-(1S,2S,R_S)-1-dimethylphosphono-2-(p-tolylsulfinyl)cyclopropane-1-carboxylate

There total 2 articles about tert-butyl (-)-(1S,2S,R_S)-1-dimethylphosphono-2-(p-tolylsulfinyl)cyclopropane-1-carboxylate 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:

(S)-dimethylsulfonium-(p-tolylsulfinyl)methyl tetrafluoroborate + tert-butyl 2-(dimethylphosphono)acrylate → tert-butyl (+)-(1R,2S,RS)-1-dimethylphosphono-2-(p-tolylsulfinyl)cyclopropane-1-carboxylate (1422157-33-2) + tert-butyl (-)-(1S,2S,RS)-1-dimethylphosphono-2-(p-tolylsulfinyl)cyclopropane-1-carboxylate (1422157-39-8) + tert-butyl (1S,2R,RS)-1-dimethylphosphono-2-(p-tolylsulfinyl)cyclopropane-1-carboxylate (1422157-40-1)

Guidance literature:

With potassium carbonate; In dichloromethane;

DOI:10.1016/j.tetlet.2012.11.002

Reference yield:

(S)-dimethylsulfonium-(p-tolylsulfinyl)methyl tetrafluoroborate + tert-butyl 2-(dimethylphosphono)acrylate → tert-butyl (+)-(1R,2S,RS)-1-dimethylphosphono-2-(p-tolylsulfinyl)cyclopropane-1-carboxylate (1422157-33-2) + tert-butyl (-)-(1S,2S,RS)-1-dimethylphosphono-2-(p-tolylsulfinyl)cyclopropane-1-carboxylate (1422157-39-8)

Guidance literature:

With potassium carbonate; In dichloromethane; at 20 ℃; Reagent/catalyst; Overall yield = 95 %; Inert atmosphere;

DOI:10.1002/ejoc.201600111

Reference yield:

tert-butyl (-)-(1S,2S,RS)-1-dimethylphosphono-2-(p-tolylsulfinyl)cyclopropane-1-carboxylate (1422157-39-8) → tert-butyl (1S,2S)-1-dimethylphosphono-2-(p-tolylsulfonyl)-2-methylcyclopropane-1-carboxylate

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 0.25 h / -70 °C / Inert atmosphere

1.2: -70 °C / Inert atmosphere

2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / Inert atmosphere

With 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1002/ejoc.201600111

Downstream raw materials:

tert-butyl (1S,2R,R_S)-1-dimethylphosphono-2-(p-tolylsulfinyl)cyclopropane-1-carboxylate

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