(5S,8E,10E,12R)-methyl 5,12-bis<(tert-butyldiphenylsilyl)oxy>-8,10-eicosadiene-6,14-diynoate

Base Information

• Chemical Name: (5S,8E,10E,12R)-methyl 5,12-bis<(tert-butyldiphenylsilyl)oxy>-8,10-eicosadiene-6,14-diynoate
• CAS No.: 90108-34-2
• Molecular Formula: C₅₃H₆₆O₄Si₂
• Molecular Weight: 823.276
• Mol file: 90108-34-2.mol

Synonyms:(5S,8E,10E,12R)-methyl 5,12-bis<(tert-butyldiphenylsilyl)oxy>-8,10-eicosadiene-6,14-diynoate

Chemical Property of (5S,8E,10E,12R)-methyl 5,12-bis<(tert-butyldiphenylsilyl)oxy>-8,10-eicosadiene-6,14-diynoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,8E,10E,12R)-methyl 5,12-bis<(tert-butyldiphenylsilyl)oxy>-8,10-eicosadiene-6,14-diynoate

There total 18 articles about (5S,8E,10E,12R)-methyl 5,12-bis<(tert-butyldiphenylsilyl)oxy>-8,10-eicosadiene-6,14-diynoate 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:

methyl 4-(chlorocarbonyl)butyrate (1501-26-4) → (5S,8E,10E,12R)-methyl 5,12-bis<(tert-butyldiphenylsilyl)oxy>-8,10-eicosadiene-6,14-diynoate (90108-34-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 1) n-BuLi, 2) CuCl / 1) THF, hexane, -78 deg C, 20 min, 2) THF, a) -78 deg C, 45 min, b) to 5 deg C

2: S-Alpine-borane / tetrahydrofuran / 15 h / 23 °C

3: 99 percent / imidazole / dimethylformamide / 2.5 h / 23 °C

4: 82 percent / Br₂, 1,2-bis(diphenylphosphino)ethane / CH₂Cl₂ / 0.08 h / 0 °C

5: 1) NaN(SiMe₃)2 / 1) THF, -10 deg C, 15 min, 2) THF, -10 deg C, 1 h

6: 1) LiN(SiMe₃)2 / 1) THF, -78 deg C, 1 h, 2) THF, a) -78 deg C, 1 h, b) -20 deg C, 1 h, c) 0 deg C, 1 h

With 1H-imidazole; n-butyllithium; (-)-(S)-alpine-borane; bromine; sodium hexamethyldisilazane; 1,2-bis-(diphenylphosphino)ethane; copper(l) chloride; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00065a012

Reference yield:

(2R)-2-<(tert-butyldiphenylsilyl)oxy>-4-decyn-1-ol (90108-33-1) → (5S,8E,10E,12R)-methyl 5,12-bis<(tert-butyldiphenylsilyl)oxy>-8,10-eicosadiene-6,14-diynoate (90108-34-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / tetra-n-propylammonium perruthenate, N-methylmorpholine N-oxide, 4A-molecular sieves / CH₂Cl₂ / 23 °C

2: 84 percent / benzene / 15 h / 60 °C

3: 1) LiN(SiMe₃)2 / 1) THF, -78 deg C, 1 h, 2) THF, a) -78 deg C, 1 h, b) -20 deg C, 1 h, c) 0 deg C, 1 h

With tetrapropylammonium perruthennate; 4 A molecular sieve; 4-methylmorpholine N-oxide; lithium hexamethyldisilazane; In dichloromethane; benzene;

DOI:10.1021/jo00065a012

Reference yield:

(5S)-5-t-butyl diphenyl silyloxy-hept-6-ynoic acid, methyl ester (90108-29-5) → (5S,8E,10E,12R)-methyl 5,12-bis<(tert-butyldiphenylsilyl)oxy>-8,10-eicosadiene-6,14-diynoate (90108-34-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 93 percent / Et₂NH, Pd(PPh₃)4, CuI / 15 h / Ambient temperature

2: 92 percent / PPh₃, CBr₄ / CH₂Cl₂ / -40 - 0 °C

3: 81 percent / aq. AcOH / tetrahydrofuran / 45 °C

4: 75 percent / CrO₃/pyridine / CH₂Cl₂ / 0 °C

5: LDA / tetrahydrofuran / -78 deg C, 8 h; -20 deg C, 1 h; room temp., 1 h

With pyridine; chromium(VI) oxide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; carbon tetrabromide; acetic acid; diethylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00324a024

upstream raw materials:

(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

(2E,4R)-4-<(tert-butyldiphenylsilyl)oxy>-2-dodecen-6-ynal

(5S)-methyl 8-(dimethylphosphono)-5-<(tert-butyldiphenylsilyl)oxy>-6-octynoate

Downstream raw materials:

Methyl (5S,6Z,8E,10E,12R,14Z)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoate

Leukotriene B

(5S,6Z,8E,10E,12R,14Z)-methyl 5,12-bis<(tert-butyldiphenylsilyl)oxy>-6,8,10,14-eicosatetraenoate

(8E,10E,14Z)-(5S,12R)-5,12-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-8,10,14-trien-6-ynoic acid methyl ester