(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

Base Information

• Chemical Name: (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
• CAS No.: 870290-88-3
• Molecular Formula: C₂₇H₃₉NO₄SSi
• Molecular Weight: 501.762
• Mol file: 870290-88-3.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 7 articles about (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 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:

tert-butyl-dimethyl-(2-methyl-1-methylene-hex-2-en-4-ynyloxy)-silane (264921-02-0) → (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)

Guidance literature:

Multi-step reaction with 3 steps

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

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

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

With silver hexafluoroantimonate; n-butyllithium; potassium hexamethylsilazane; 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline]; copper dichloride; In tetrahydrofuran; hexane; dichloromethane; toluene; 1: Diels-Alder reaction;

DOI:10.1021/ol051840r

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (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)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1021/ol051840r

Reference yield:

(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 (870290-79-2) → (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)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With n-butyllithium; potassium hexamethylsilazane; In tetrahydrofuran; hexane; toluene;

DOI:10.1021/ol051840r

upstream raw materials:

(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

t-butyldimethylsiyl triflate

tert-butyl-dimethyl-(2-methyl-1-methylene-hex-2-en-4-ynyloxy)-silane

3-methylidene-2-oxo-piperidine

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}-4-methyl-benzenesulfonamide

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

C₂₇H₄₀INO₄SSi

C₄₉H₈₃NO₆SSi₂