6-Heptynoic acid, 5-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-, methyl ester, (S)-

Base Information

• Chemical Name: 6-Heptynoic acid, 5-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-, methyl ester, (S)-
• CAS No.: 90108-29-5
• Molecular Formula: C24H30O3Si
• Molecular Weight: 394.586
• Mol file: 90108-29-5.mol

Synonyms:

Chemical Property of 6-Heptynoic acid, 5-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-, methyl ester, (S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-Heptynoic acid, 5-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-, methyl ester, (S)-

There total 8 articles about 6-Heptynoic acid, 5-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-, methyl ester, (S)- 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: 96.0%

(5S)-5-hydroxy-hept-6-ynoic acid, methyl ester (90108-28-4) + tert-butylchlorodiphenylsilane (58479-61-1) → (5S)-5-t-butyl diphenyl silyloxy-hept-6-ynoic acid, methyl ester (90108-29-5)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide;

DOI:10.1021/ja00324a024

Reference yield:

(S)-5-hydroxy-7-trimethylsilylhept-6-ynoic acid methyl ester (120085-71-4,90108-27-3) → (5S)-5-t-butyl diphenyl silyloxy-hept-6-ynoic acid, methyl ester (90108-29-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1.5 h

2: 74 percent / imidazole / dimethylformamide / 48 h / Ambient temperature

With 1H-imidazole; tetrabutyl ammonium fluoride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/0040-4020(96)00316-X

Reference yield:

methyl 4-(chlorocarbonyl)butyrate (1501-26-4) → (5S)-5-t-butyl diphenyl silyloxy-hept-6-ynoic acid, methyl ester (90108-29-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 60 percent / AlCl₃ / CH₂Cl₂ / 0 °C

2: 85 percent / (-)-9-pinanyl-BBN / tetrahydrofuran / 25 °C

3: 80 percent / KF_.2H₂O / dimethylformamide

4: 96 percent / imidazole / dimethylformamide

With 1H-imidazole; potassium fluoride; aluminium trichloride; (-)-9-pinanyl-BBN; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00324a024

upstream raw materials:

(5S)-5-hydroxy-hept-6-ynoic acid, methyl ester

tert-butylchlorodiphenylsilane

methyl 4-formylbutanoate

(S)-5-hydroxy-7-trimethylsilylhept-6-ynoic acid methyl ester

Downstream raw materials:

methyl 5(S)-(tert-butyldiphenylsiloxy)-10-hydroxydec-8-en-6-ynoate

(E)-(S)-5-(tert-Butyl-diphenyl-silanyloxy)-7-iodo-hept-6-enoic acid methyl ester

methyl (6Z,10E,12E,5S,14R,15S)-5-(tert-butyldiphenylsiloxy)-14,15-bis(tert-butyldimethylsiloxy)-6,10,12-eicosatrien-8-ynoate

methyl (5S)-7-iodo-5-(tert-butyldiphenylsiloxy)hept-6-enoate