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

Base Information

• Chemical Name: methyl 5(S)-(tert-butyldiphenylsiloxy)-10-hydroxydec-8-en-6-ynoate
• CAS No.: 90108-30-8
• Molecular Formula: C₂₇H₃₄O₄Si
• Molecular Weight: 450.65
• Mol file: 90108-30-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about methyl 5(S)-(tert-butyldiphenylsiloxy)-10-hydroxydec-8-en-6-ynoate 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: 93.0%

(E)-3-bromoprop-2-en-1-ol (37428-55-0) + (5S)-5-t-butyl diphenyl silyloxy-hept-6-ynoic acid, methyl ester (90108-29-5) → methyl 5(S)-(tert-butyldiphenylsiloxy)-10-hydroxydec-8-en-6-ynoate (90108-30-8)

Guidance literature:

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diethylamine; for 15h; Ambient temperature;

DOI:10.1021/ja00324a024

Reference yield:

methyl 4-(chlorocarbonyl)butyrate (1501-26-4) → methyl 5(S)-(tert-butyldiphenylsiloxy)-10-hydroxydec-8-en-6-ynoate (90108-30-8)

Guidance literature:

Multi-step reaction with 5 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

5: 93 percent / Et₂NH, Pd(PPh₃)4, CuI / 15 h / Ambient temperature

With 1H-imidazole; potassium fluoride; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; aluminium trichloride; (-)-9-pinanyl-BBN; diethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00324a024

Reference yield:

(5S)-5-hydroxy-hept-6-ynoic acid, methyl ester (90108-28-4) → methyl 5(S)-(tert-butyldiphenylsiloxy)-10-hydroxydec-8-en-6-ynoate (90108-30-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / imidazole / dimethylformamide

2: 93 percent / Et₂NH, Pd(PPh₃)4, CuI / 15 h / Ambient temperature

With 1H-imidazole; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diethylamine; In N,N-dimethyl-formamide;

DOI:10.1021/ja00324a024

upstream raw materials:

(E)-3-bromoprop-2-en-1-ol

(5S)-5-t-butyl diphenyl silyloxy-hept-6-ynoic acid, methyl ester

methyl 4-(chlorocarbonyl)butyrate

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

Downstream raw materials:

(E)-(S)-10-Bromo-5-(tert-butyl-diphenyl-silanyloxy)-dec-8-en-6-ynoic acid methyl ester

Leukotriene B

(2R)-2-<(tert-butyldiphenylsilyl)oxy>-4-decynal

(E)-(S)-5-(tert-Butyl-diphenyl-silanyloxy)-10-(dimethoxy-phosphoryl)-dec-8-en-6-ynoic acid methyl ester