(6Z,8E,10E,14Z)-(3R,5S,12R)-3,12-Bis-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-icosa-6,8,10,14-tetraenoic acid methyl ester

Base Information

• Chemical Name: (6Z,8E,10E,14Z)-(3R,5S,12R)-3,12-Bis-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-icosa-6,8,10,14-tetraenoic acid methyl ester
• CAS No.: 158800-23-8
• Molecular Formula: C₅₃H₇₀O₅Si₂
• Molecular Weight: 843.307
• Mol file: 158800-23-8.mol

Synonyms:(6Z,8E,10E,14Z)-(3R,5S,12R)-3,12-Bis-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-icosa-6,8,10,14-tetraenoic acid methyl ester

Chemical Property of (6Z,8E,10E,14Z)-(3R,5S,12R)-3,12-Bis-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-icosa-6,8,10,14-tetraenoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6Z,8E,10E,14Z)-(3R,5S,12R)-3,12-Bis-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-icosa-6,8,10,14-tetraenoic acid methyl ester

There total 10 articles about (6Z,8E,10E,14Z)-(3R,5S,12R)-3,12-Bis-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-icosa-6,8,10,14-tetraenoic acid methyl ester 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: 100.0%

methanol (67-56-1) + 3(R),12(R)-bis<(tert-butyldiphenylsilyl)oxy>-5(S)-hydroxy-6(Z),8(E),10(E),14(Z)-eicosatetranoic δ-lactone (158719-04-1) → (6Z,8E,10E,14Z)-(3R,5S,12R)-3,12-Bis-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-icosa-6,8,10,14-tetraenoic acid methyl ester (158800-23-8)

Guidance literature:

With triethylamine; at 24 ℃; for 1h;

DOI:10.1021/ja00091a004

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (6Z,8E,10E,14Z)-(3R,5S,12R)-3,12-Bis-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-icosa-6,8,10,14-tetraenoic acid methyl ester (158800-23-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 70 percent / pyridine, AgNO₃ / tetrahydrofuran / 3 h / 23 °C

2: 97 percent / pyridine / CH₂Cl₂ / 2 h / -20 °C

3: 53 percent / DBU / 0.5 h / 23 °C

4: 1.) t-BuLi, 2.) n-Bu₃SnCl, 3.) Pd(PPh₃)4

5: 79 percent / Rieke Zn / tetrahydrofuran; methanol; H₂O / 3 h / Heating

6: 67 percent / 6percent methanolic HCl, NaBH₃CN / ethanol / 3 h / Ambient temperature

7: aq. AcOH / tetrahydrofuran / 5 h / 60 °C

8: pyridinium chlorochromate, Al₂O₃ / CH₂Cl₂ / 2 h / 24 °C

9: 100 percent / Et₃N / 1 h / 24 °C

With pyridine; hydrogenchloride; aluminum oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tributyltin chloride; tert.-butyl lithium; sodium cyanoborohydride; silver nitrate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; pyridinium chlorochromate; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; water;

DOI:10.1021/ja00091a004

Reference yield:

(3R,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-3-ol (158719-05-2) → (6Z,8E,10E,14Z)-(3R,5S,12R)-3,12-Bis-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-icosa-6,8,10,14-tetraenoic acid methyl ester (158800-23-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 97 percent / pyridine / CH₂Cl₂ / 2 h / -20 °C

2: 53 percent / DBU / 0.5 h / 23 °C

3: 1.) t-BuLi, 2.) n-Bu₃SnCl, 3.) Pd(PPh₃)4

4: 79 percent / Rieke Zn / tetrahydrofuran; methanol; H₂O / 3 h / Heating

5: 67 percent / 6percent methanolic HCl, NaBH₃CN / ethanol / 3 h / Ambient temperature

6: aq. AcOH / tetrahydrofuran / 5 h / 60 °C

7: pyridinium chlorochromate, Al₂O₃ / CH₂Cl₂ / 2 h / 24 °C

8: 100 percent / Et₃N / 1 h / 24 °C

With pyridine; hydrogenchloride; aluminum oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tributyltin chloride; tert.-butyl lithium; sodium cyanoborohydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; pyridinium chlorochromate; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; water;

DOI:10.1021/ja00091a004

upstream raw materials:

methanol

3(R),12(R)-bis<(tert-butyldiphenylsilyl)oxy>-5(S)-hydroxy-6(Z),8(E),10(E),14(Z)-eicosatetranoic δ-lactone

tert-butylchlorodiphenylsilane

2(R)-methoxy-4(S)-<(tert-butyldiphenylsilyl)oxy>-2,3-dihydro-4H-pyran