(S_S,2S,3S)-(+)-N-methoxy-N,2-dimethyl-3-(2,4,6-triisopropylphenylsulfinylamino)pentanamide

Base Information

• Chemical Name: (S_S,2S,3S)-(+)-N-methoxy-N,2-dimethyl-3-(2,4,6-triisopropylphenylsulfinylamino)pentanamide
• CAS No.: 943241-49-4
• Molecular Formula: C₂₃H₄₀N₂O₃S
• Molecular Weight: 424.648

Synonyms:(S_S,2S,3S)-(+)-N-methoxy-N,2-dimethyl-3-(2,4,6-triisopropylphenylsulfinylamino)pentanamide

Chemical Property of (S_S,2S,3S)-(+)-N-methoxy-N,2-dimethyl-3-(2,4,6-triisopropylphenylsulfinylamino)pentanamide

Chemical Property:

Purity/Quality:

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Technology Process of (S_S,2S,3S)-(+)-N-methoxy-N,2-dimethyl-3-(2,4,6-triisopropylphenylsulfinylamino)pentanamide

There total 2 articles about (S_S,2S,3S)-(+)-N-methoxy-N,2-dimethyl-3-(2,4,6-triisopropylphenylsulfinylamino)pentanamide 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: 80.0%

(S)-(+)-N-propylidene-2,4,6-triisopropylbenzenesulfinamide (943241-36-9) + N-methyl-N-methoxypropionamide (104863-65-2) → (SS,2S,3S)-(+)-N-methoxy-N,2-dimethyl-3-(2,4,6-triisopropylphenylsulfinylamino)pentanamide (943241-49-4) + (SS,2R,3S)-(+)-N-methoxy-N,2-dimethyl-3-(2,4,6-triisopropylphenylsulfinylamino)pentanamide (943241-42-7)

Guidance literature:

N-methyl-N-methoxypropionamide; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 2h;

(S)-(+)-N-propylidene-2,4,6-triisopropylbenzenesulfinamide; In tetrahydrofuran; at -78 ℃; Further stages.;

DOI:10.1021/ol0708166

Reference yield:

(S)-(+)-2,4,6-triisopropylbenzenesulfinamide (669091-08-1) → (SS,2S,3S)-(+)-N-methoxy-N,2-dimethyl-3-(2,4,6-triisopropylphenylsulfinylamino)pentanamide (943241-49-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 85 percent / Ti(OEt)4 / CH₂Cl₂ / cooling

2.1: LiHMDS / tetrahydrofuran / 2 h / -78 °C

2.2: 20 percent / tetrahydrofuran / -78 °C

With lithium hexamethyldisilazane; titanium(IV) tetraethanolate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol0708166

Reference yield:

(SS,2S,3S)-(+)-N-methoxy-N,2-dimethyl-3-(2,4,6-triisopropylphenylsulfinylamino)pentanamide (943241-49-4) → (3S,4S)-(-)-4-ethyl-3-methyl-1-tosylazetidin-2-one

Guidance literature:

Multi-step reaction with 4 steps

1: HCl / methanol; diethyl ether / 0.5 h / 0 °C

2: 0.036 g / Et₃N; DMAP / CH₂Cl₂ / 2 h / 0 °C

3: 95 percent / aq. KOH / ethanol / 60 h / Heating

4: 67 percent / DCC; 4-pyrrolidinopyridine / CH₂Cl₂ / 18 h / 20 °C

With hydrogenchloride; dmap; potassium hydroxide; 4-pyrrolidin-1-ylpyridine; triethylamine; dicyclohexyl-carbodiimide; In methanol; diethyl ether; ethanol; dichloromethane;

DOI:10.1021/ol0708166

upstream raw materials:

(S)-(+)-N-propylidene-2,4,6-triisopropylbenzenesulfinamide

N-methyl-N-methoxypropionamide

(S)-(+)-2,4,6-triisopropylbenzenesulfinamide

Downstream raw materials:

(2S,3S)-(-)-N-methoxy-N,2-dimethyl-3-(4-methylphenylsulfonamido)pentanamide

(2S,3S)-(+)-2-methyl-3-(4-methylphenylsulfonamido)pentanoic acid

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