(S_R,R)-(+)-methyl 3-(p-tolylsulfinamido)-3-([4-allyldimethylsilyl]phenyl)propanoate

Base Information

• Chemical Name: (S_R,R)-(+)-methyl 3-(p-tolylsulfinamido)-3-([4-allyldimethylsilyl]phenyl)propanoate
• CAS No.: 359792-69-1
• Molecular Formula: C₂₂H₂₉NO₃SSi
• Molecular Weight: 415.629

Synonyms:(S_R,R)-(+)-methyl 3-(p-tolylsulfinamido)-3-([4-allyldimethylsilyl]phenyl)propanoate

Chemical Property of (S_R,R)-(+)-methyl 3-(p-tolylsulfinamido)-3-([4-allyldimethylsilyl]phenyl)propanoate

Chemical Property:

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Technology Process of (S_R,R)-(+)-methyl 3-(p-tolylsulfinamido)-3-([4-allyldimethylsilyl]phenyl)propanoate

There total 5 articles about (S_R,R)-(+)-methyl 3-(p-tolylsulfinamido)-3-([4-allyldimethylsilyl]phenyl)propanoate 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: 72.0%

acetic acid methyl ester (79-20-9) + (S)-(+)-N-(4-allyldimethylsilylbenzylidene)-p-toluenesulfonamide (359792-68-0) → (SR,R)-(+)-methyl 3-(p-tolylsulfinamido)-3-([4-allyldimethylsilyl]phenyl)propanoate (359792-69-1)

Guidance literature:

acetic acid methyl ester; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h;

(S)-(+)-N-(4-allyldimethylsilylbenzylidene)-p-toluenesulfonamide; In diethyl ether; at -78 ℃; for 7h;

DOI:10.1016/S0040-4020(01)00457-4

Reference yield:

Allylchlorodimethylsilane (4028-23-3) → (SR,R)-(+)-methyl 3-(p-tolylsulfinamido)-3-([4-allyldimethylsilyl]phenyl)propanoate (359792-69-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 82 percent / tetrahydrofuran / 1 h / 20 °C

2.1: t-BuLi / tetrahydrofuran; pentane

2.2: 82 percent / 1 h / -78 - 20 °C

3.1: LiHMDS / tetrahydrofuran / -78 - 20 °C

3.2: 47 percent / CsF / tetrahydrofuran / 20 °C

4.1: NaHMDS / tetrahydrofuran / 0.5 h / -78 °C

4.2: 72 percent / diethyl ether / 7 h / -78 °C

With n-butyllithium; tert.-butyl lithium; sodium hexamethyldisilazane; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; pentane;

DOI:10.1016/S0040-4020(01)00457-4

Reference yield:

1.4-dibromobenzene (106-37-6) → (SR,R)-(+)-methyl 3-(p-tolylsulfinamido)-3-([4-allyldimethylsilyl]phenyl)propanoate (359792-69-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 82 percent / tetrahydrofuran / 1 h / 20 °C

2.1: t-BuLi / tetrahydrofuran; pentane

2.2: 82 percent / 1 h / -78 - 20 °C

3.1: LiHMDS / tetrahydrofuran / -78 - 20 °C

3.2: 47 percent / CsF / tetrahydrofuran / 20 °C

4.1: NaHMDS / tetrahydrofuran / 0.5 h / -78 °C

4.2: 72 percent / diethyl ether / 7 h / -78 °C

With n-butyllithium; tert.-butyl lithium; sodium hexamethyldisilazane; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; pentane;

DOI:10.1016/S0040-4020(01)00457-4

upstream raw materials:

acetic acid methyl ester

(S)-(+)-N-(4-allyldimethylsilylbenzylidene)-p-toluenesulfonamide

Allylchlorodimethylsilane

1.4-dibromobenzene

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