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

Base Information

• Chemical Name: 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
• CAS No.: 144318-30-9
• Molecular Formula: C₃₇H₄₈BrNO₅S₂Si
• Molecular Weight: 758.913
• Mol file: 144318-30-9.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 9 articles about 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 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: 83.0%

2-Bromo-6-methoxy-3-((E)-2-phenylsulfanyl-vinyl)-phenol (144318-29-6) + N-{2-[(5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-hydroxy-cyclohex-1-enyl]-ethyl}-4,N-dimethyl-benzenesulfonamide (144318-32-1) → 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 (144318-30-9)

Guidance literature:

With tributylphosphine; In tetrahydrofuran; at 0 ℃;

DOI:10.1021/ja00050a075

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → 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 (144318-30-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / i-Pr₂NEt / -78 °C

2: 83 percent / PBu₃, DAED / tetrahydrofuran / 0 °C

With tributylphosphine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran;

DOI:10.1021/ja00050a075

Reference yield:

4-Methyl-N-[2-(3-oxo-cyclohex-1-enyl)-ethyl]-benzenesulfonamide (144318-24-1) → 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 (144318-30-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 96 percent / K₂CO₃ / acetone

2: 97 percent / NaBH₄, CeCl₃ / methanol / 0 °C

3: 92 percent / m-CPBA / CH₂Cl₂ / 0 °C

4: 85 percent / Ti(OiPr)4 / benzene / 70 °C

5: 82 percent / i-Pr₂NEt / -78 °C

6: 83 percent / PBu₃, DAED / tetrahydrofuran / 0 °C

With titanium(IV) isopropylate; sodium tetrahydroborate; cerium(III) chloride; tributylphosphine; potassium carbonate; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; acetone; benzene;

DOI:10.1021/ja00050a075

upstream raw materials:

2-Bromo-6-methoxy-3-((E)-2-phenylsulfanyl-vinyl)-phenol

N-{2-[(5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-hydroxy-cyclohex-1-enyl]-ethyl}-4,N-dimethyl-benzenesulfonamide

t-butyldimethylsiyl triflate

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

Downstream raw materials:

N-[2-((3R,3aR,9aS,9bS)-3-Hydroxy-5-methoxy-1,3,3a,9a-tetrahydro-2H-phenanthro[4,5-bcd]furan-9b-yl)-ethyl]-4,N-dimethyl-benzenesulfonamide

(+/-)-dihydroisocodeine

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

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