(-)-(3S,3aR,6S,6aS)-1,6-dimethyl-5-[(3R)-3-methylpentanoyl]-3-phenylhexahydroisothiazolo[4,5-c]isoxazole 4,4-dioxide

Base Information

• Chemical Name: (-)-(3S,3aR,6S,6aS)-1,6-dimethyl-5-[(3R)-3-methylpentanoyl]-3-phenylhexahydroisothiazolo[4,5-c]isoxazole 4,4-dioxide
• CAS No.: 500707-23-3
• Molecular Formula: C₁₈H₂₆N₂O₄S
• Molecular Weight: 366.481
• Mol file: 500707-23-3.mol

Synonyms:

Chemical Property of (-)-(3S,3aR,6S,6aS)-1,6-dimethyl-5-[(3R)-3-methylpentanoyl]-3-phenylhexahydroisothiazolo[4,5-c]isoxazole 4,4-dioxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(3S,3aR,6S,6aS)-1,6-dimethyl-5-[(3R)-3-methylpentanoyl]-3-phenylhexahydroisothiazolo[4,5-c]isoxazole 4,4-dioxide

There total 5 articles about (-)-(3S,3aR,6S,6aS)-1,6-dimethyl-5-[(3R)-3-methylpentanoyl]-3-phenylhexahydroisothiazolo[4,5-c]isoxazole 4,4-dioxide 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%

ethylmagnesium chloride (2386-64-3) + (-)-(3S,3aR,6S,6aS)-5-[(2E)-but-2-enoyl]-1,6-dimethyl-3-phenylhexahydroisothiazolo[4,5-c]isoxazole 4,4-dioxide (500707-19-7) → (-)-(3S,3aR,6S,6aS)-1,6-dimethyl-5-[(3R)-3-methylpentanoyl]-3-phenylhexahydroisothiazolo[4,5-c]isoxazole 4,4-dioxide (500707-23-3) + (-)-(3S,3aR,6S,6aS)-1,6-dimethyl-5-[(3S)-3-methylpentanoyl]-3-phenylhexahydroisothiazolo[4,5-c]isoxazole 4,4-dioxide

Guidance literature:

In tetrahydrofuran; diethyl ether; at -80 - -60 ℃;

DOI:10.1016/S0957-4166(02)00465-2

Reference yield:

trans 2-phenylethenesulfonyl chloride (52147-97-4) → (-)-(3S,3aR,6S,6aS)-1,6-dimethyl-5-[(3R)-3-methylpentanoyl]-3-phenylhexahydroisothiazolo[4,5-c]isoxazole 4,4-dioxide (500707-23-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 91 percent / Et₃N / CH₂Cl₂ / 16.5 h / 0 - 25 °C

2.1: 85 percent / Dess-Martin periodinane / CH₂Cl₂; H₂O / 0.5 h

3.1: 78 percent / Et₃N / ethanol / 24 h / Heating

4.1: NaH / toluene / 2 h

4.2: 88 percent / toluene / 18 h

5.1: 81 percent / tetrahydrofuran; diethyl ether / -80 - -60 °C

With sodium hydride; Dess-Martin periodane; triethylamine; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; toluene; 5.1: asymmetric Grignard addition;

DOI:10.1016/S0957-4166(02)00465-2

Reference yield:

(E)-(-)-N-[(1S)-2-hydroxy-1-methylethyl]-2-phenylethylenesulfonamide (500707-11-9) → (-)-(3S,3aR,6S,6aS)-1,6-dimethyl-5-[(3R)-3-methylpentanoyl]-3-phenylhexahydroisothiazolo[4,5-c]isoxazole 4,4-dioxide (500707-23-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 85 percent / Dess-Martin periodinane / CH₂Cl₂; H₂O / 0.5 h

2.1: 78 percent / Et₃N / ethanol / 24 h / Heating

3.1: NaH / toluene / 2 h

3.2: 88 percent / toluene / 18 h

4.1: 81 percent / tetrahydrofuran; diethyl ether / -80 - -60 °C

With sodium hydride; Dess-Martin periodane; triethylamine; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; toluene; 4.1: asymmetric Grignard addition;

DOI:10.1016/S0957-4166(02)00465-2

upstream raw materials:

ethylmagnesium chloride

(-)-(3S,3aR,6S,6aS)-5-[(2E)-but-2-enoyl]-1,6-dimethyl-3-phenylhexahydroisothiazolo[4,5-c]isoxazole 4,4-dioxide

trans 2-phenylethenesulfonyl chloride

(E)-(+)-N-[(1S)-1-methyl-2-oxoethyl]-2-phenylethylenesulfonamide

Downstream raw materials:

(R)-3-methylpentanoic acid