N-[2-((5R,6S)-5,6-Dihydroxy-cyclohex-1-enyl)-ethyl]-4,N-dimethyl-benzenesulfonamide

Base Information

• Chemical Name: N-[2-((5R,6S)-5,6-Dihydroxy-cyclohex-1-enyl)-ethyl]-4,N-dimethyl-benzenesulfonamide
• CAS No.: 144318-28-5
• Molecular Formula: C₁₆H₂₃NO₄S
• Molecular Weight: 325.429
• Mol file: 144318-28-5.mol

Synonyms:N-[2-((5R,6S)-5,6-Dihydroxy-cyclohex-1-enyl)-ethyl]-4,N-dimethyl-benzenesulfonamide

Chemical Property of N-[2-((5R,6S)-5,6-Dihydroxy-cyclohex-1-enyl)-ethyl]-4,N-dimethyl-benzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[2-((5R,6S)-5,6-Dihydroxy-cyclohex-1-enyl)-ethyl]-4,N-dimethyl-benzenesulfonamide

There total 12 articles about N-[2-((5R,6S)-5,6-Dihydroxy-cyclohex-1-enyl)-ethyl]-4,N-dimethyl-benzenesulfonamide 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: 85.0%

N-[2-((1S,5S,6S)-5-Hydroxy-7-oxa-bicyclo[4.1.0]hept-1-yl)-ethyl]-4,N-dimethyl-benzenesulfonamide (144318-27-4) → N-[2-((5R,6S)-5,6-Dihydroxy-cyclohex-1-enyl)-ethyl]-4,N-dimethyl-benzenesulfonamide (144318-28-5)

Guidance literature:

With titanium(IV) isopropylate; In benzene; at 70 ℃;

DOI:10.1021/ja00050a075

Reference yield:

N-[2-(3-Hydroxy-cyclohex-1-enyl)-ethyl]-4,N-dimethyl-benzenesulfonamide (144318-26-3) → N-[2-((5R,6S)-5,6-Dihydroxy-cyclohex-1-enyl)-ethyl]-4,N-dimethyl-benzenesulfonamide (144318-28-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.09 g / m-CPBA / CH₂Cl₂ / 2 h / 0 °C

2: 85 percent / Ti(OiPr)4 / benzene / 2 h / Heating

With titanium(IV) isopropylate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; benzene;

DOI:10.1021/jo0513008

Reference yield:

4-Methyl-N-[2-(3-oxo-cyclohex-1-enyl)-ethyl]-benzenesulfonamide (144318-24-1) → N-[2-((5R,6S)-5,6-Dihydroxy-cyclohex-1-enyl)-ethyl]-4,N-dimethyl-benzenesulfonamide (144318-28-5)

Guidance literature:

Multi-step reaction with 4 steps

1: anhydrous K₂CO₃ / acetone / 24 h / 20 °C

2: NaBH₄; CeCl₃*7H₂O / CH₂Cl₂; methanol / 0.5 h / 0 °C

3: 2.09 g / m-CPBA / CH₂Cl₂ / 2 h / 0 °C

4: 85 percent / Ti(OiPr)4 / benzene / 2 h / Heating

With titanium(IV) isopropylate; sodium tetrahydroborate; cerium(III) chloride; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane; acetone; benzene; 2: Luche reduction;

DOI:10.1021/jo0513008

upstream raw materials:

N-[2-((1S,5S,6S)-5-Hydroxy-7-oxa-bicyclo[4.1.0]hept-1-yl)-ethyl]-4,N-dimethyl-benzenesulfonamide

2-(5-methoxy-cyclohexa-1,4-dienyl)-ethylamine

N-[2-(3-Hydroxy-cyclohex-1-enyl)-ethyl]-4,N-dimethyl-benzenesulfonamide

4-Methyl-N-[2-(3-oxo-cyclohex-1-enyl)-ethyl]-benzenesulfonamide

Downstream raw materials:

(+/-)-dihydroisocodeine

(+/-)-dihydrocodeine

N-{2-[(5R,6R)-6-[2-Bromo-6-methoxy-3-((E)-2-phenylsulfanyl-vinyl)-phenoxy]-5-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enyl]-ethyl}-4,N-dimethyl-benzenesulfonamide

N-(2-{(5S,6S)-6-[2-Bromo-6-methoxy-3-((E)-2-phenylsulfanyl-vinyl)-phenoxy]-5-hydroxy-cyclohex-1-enyl}-ethyl)-4,N-dimethyl-benzenesulfonamide