N-{3-[4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-1-(5-methyl-hex-4-enoyl)-2-prop-1-ynyl-cyclohex-3-enyl]-propyl}-4-methyl-benzenesulfonamide

Base Information

• Chemical Name: N-{3-[4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-1-(5-methyl-hex-4-enoyl)-2-prop-1-ynyl-cyclohex-3-enyl]-propyl}-4-methyl-benzenesulfonamide
• CAS No.: 870290-84-9
• Molecular Formula: C₃₃H₅₁NO₄SSi
• Molecular Weight: 585.924
• Mol file: 870290-84-9.mol

Synonyms:N-{3-[4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-1-(5-methyl-hex-4-enoyl)-2-prop-1-ynyl-cyclohex-3-enyl]-propyl}-4-methyl-benzenesulfonamide

Chemical Property of N-{3-[4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-1-(5-methyl-hex-4-enoyl)-2-prop-1-ynyl-cyclohex-3-enyl]-propyl}-4-methyl-benzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-{3-[4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-1-(5-methyl-hex-4-enoyl)-2-prop-1-ynyl-cyclohex-3-enyl]-propyl}-4-methyl-benzenesulfonamide

There total 11 articles about N-{3-[4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-1-(5-methyl-hex-4-enoyl)-2-prop-1-ynyl-cyclohex-3-enyl]-propyl}-4-methyl-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: 63.0%

(6S,7S)-9-(tert-Butyl-dimethyl-silanyloxy)-8-methyl-7-prop-1-ynyl-2-(toluene-4-sulfonyl)-2-aza-spiro[5.5]undec-8-en-1-one (870290-88-3) + 1-bromo-4-methylpent-3-ene (2270-59-9) → N-{3-[4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-1-(5-methyl-hex-4-enoyl)-2-prop-1-ynyl-cyclohex-3-enyl]-propyl}-4-methyl-benzenesulfonamide (870290-84-9)

Guidance literature:

1-bromo-4-methylpent-3-ene; With tert.-butyl lithium; In diethyl ether; pentane; at -78 ℃; Inert atmosphere;

(6S,7S)-9-(tert-Butyl-dimethyl-silanyloxy)-8-methyl-7-prop-1-ynyl-2-(toluene-4-sulfonyl)-2-aza-spiro[5.5]undec-8-en-1-one; In tetrahydrofuran; diethyl ether; pentane; at -20 - 20 ℃; for 14h; Inert atmosphere;

DOI:10.1021/ja207385y

Reference yield:

tert-butyl-dimethyl-(2-methyl-1-methylene-hex-2-en-4-ynyloxy)-silane (264921-02-0) → N-{3-[4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-1-(5-methyl-hex-4-enoyl)-2-prop-1-ynyl-cyclohex-3-enyl]-propyl}-4-methyl-benzenesulfonamide (870290-84-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: AgSbF₆ / CuCl₂; (S,S)-2,2'-isopropylidenebis(4-tert-butyl-2-oxazoline) / CH₂Cl₂ / 10 h / 25 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C

3.1: KHMDS / tetrahydrofuran; toluene / 0.33 h / -78 °C

4.1: t-BuLi / diethyl ether; pentane / 0.08 h / -78 °C

4.2: TMEDA / diethyl ether; tetrahydrofuran; pentane / 14 h / -20 - 20 °C

With silver hexafluoroantimonate; n-butyllithium; tert.-butyl lithium; potassium hexamethylsilazane; 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline]; copper dichloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; pentane; 1.1: Diels-Alder reaction;

DOI:10.1021/ol051840r

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → N-{3-[4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-1-(5-methyl-hex-4-enoyl)-2-prop-1-ynyl-cyclohex-3-enyl]-propyl}-4-methyl-benzenesulfonamide (870290-84-9)

Guidance literature:

Multi-step reaction with 5 steps

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

1.2: 92 percent / tetrahydrofuran / 0.17 h / -78 °C

2.1: AgSbF₆ / CuCl₂; (S,S)-2,2'-isopropylidenebis(4-tert-butyl-2-oxazoline) / CH₂Cl₂ / 10 h / 25 °C

3.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C

4.1: KHMDS / tetrahydrofuran; toluene / 0.33 h / -78 °C

5.1: t-BuLi / diethyl ether; pentane / 0.08 h / -78 °C

5.2: TMEDA / diethyl ether; tetrahydrofuran; pentane / 14 h / -20 - 20 °C

With silver hexafluoroantimonate; n-butyllithium; tert.-butyl lithium; sodium hexamethyldisilazane; potassium hexamethylsilazane; 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline]; copper dichloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; pentane; 2.1: Diels-Alder reaction;

DOI:10.1021/ol051840r

upstream raw materials:

(6S,7S)-9-(tert-Butyl-dimethyl-silanyloxy)-8-methyl-7-prop-1-ynyl-2-(toluene-4-sulfonyl)-2-aza-spiro[5.5]undec-8-en-1-one

1-bromo-4-methylpent-3-ene

(6S,7S)-9-(tert-Butyl-dimethyl-silanyloxy)-8-methyl-7-prop-1-ynyl-2-aza-spiro[5.5]undec-8-en-1-one

(6S,7S)-9-(tert-Butyl-dimethyl-silanyloxy)-8-methyl-1-oxo-7-prop-1-ynyl-2-aza-spiro[5.5]undec-8-ene-2-carboxylic acid benzyl ester

Downstream raw materials:

N-{3-[4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-1-(5-methyl-hex-4-enoyl)-2-prop-1-ynyl-cyclohex-3-enyl]-propyl}-2,2,2-trifluoro-acetamide