2-Azaspiro[5.5]undec-8-ene-2-carboxylic acid, 9-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-8-methyl-1-oxo-7-(1-propynyl)-, phenylmethyl ester, (6S,7S)-

Base Information

• Chemical Name: 2-Azaspiro[5.5]undec-8-ene-2-carboxylic acid, 9-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-8-methyl-1-oxo-7-(1-propynyl)-, phenylmethyl ester, (6S,7S)-
• CAS No.: 870290-79-2
• Molecular Formula: C28H39NO4Si
• Molecular Weight: 481.707
• Mol file: 870290-79-2.mol

Synonyms:

Chemical Property of 2-Azaspiro[5.5]undec-8-ene-2-carboxylic acid, 9-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-8-methyl-1-oxo-7-(1-propynyl)-, phenylmethyl ester, (6S,7S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Azaspiro[5.5]undec-8-ene-2-carboxylic acid, 9-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-8-methyl-1-oxo-7-(1-propynyl)-, phenylmethyl ester, (6S,7S)-

There total 6 articles about 2-Azaspiro[5.5]undec-8-ene-2-carboxylic acid, 9-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-8-methyl-1-oxo-7-(1-propynyl)-, phenylmethyl ester, (6S,7S)- 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: 84.0%

tert-butyl-dimethyl-(2-methyl-1-methylene-hex-2-en-4-ynyloxy)-silane (264921-02-0) + 3-methylene-2-oxo-piperidine-1-carboxylic acid benzyl ester (440677-00-9) → (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)

Guidance literature:

With silver hexafluoroantimonate; 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline]; copper dichloride; In dichloromethane; at 20 ℃; diastereoselective reaction; Inert atmosphere; Darkness;

DOI:10.1021/ja207385y

Reference yield:

tert-butyl-dimethyl-(2-methyl-1-methylene-hex-2-en-4-ynyloxy)-silane (264921-02-0) + 3-methylene-2-oxo-piperidine-1-carboxylic acid benzyl ester (440677-00-9) → (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) + (6R,7R)-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

Guidance literature:

With silver hexafluoroantimonate; 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline]; copper dichloride; In dichloromethane; at 25 ℃; for 10h; Title compound not separated from byproducts;

DOI:10.1021/ol051840r

Reference yield:

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

Guidance literature:

Multi-step reaction with 2 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

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

DOI:10.1021/ol051840r

upstream raw materials:

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

3-methylene-2-oxo-piperidine-1-carboxylic acid benzyl ester

t-butyldimethylsiyl triflate

3-methylidene-2-oxo-piperidine

Downstream raw materials:

C₃₉H₆₇NO₄SSiSn

C₂₁H₂₅NO₄S

C₂₂H₂₄F₃NO₆S₂