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

Base Information

• Chemical Name: 3(R),12(R)-bis<(tert-butyldiphenylsilyl)oxy>-5(S)-hydroxy-6(Z),8(E),10(E),14(Z)-eicosatetranoic δ-lactone
• CAS No.: 158719-04-1
• Molecular Formula: C₅₂H₆₆O₄Si₂
• Molecular Weight: 811.265
• Mol file: 158719-04-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

(2R,4R,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-[(1Z,3E,5E,9Z)-(R)-7-(tert-butyl-diphenyl-silanyloxy)-pentadeca-1,3,5,9-tetraenyl]-tetrahydro-pyran-2-ol → 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)

Guidance literature:

With aluminum oxide; pyridinium chlorochromate; In dichloromethane; at 24 ℃; for 2h; Yield given;

DOI:10.1021/ja00091a004

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → 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)

Guidance literature:

Multi-step reaction with 7 steps

1: 95 percent / pyridine, AgNO₃ / CH₂Cl₂ / 6 h / Ambient temperature

2: 98 percent / AgNO₃, NBS / acetone / 1 h / 24 °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

With pyridine; hydrogenchloride; aluminum oxide; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tributyltin chloride; tert.-butyl lithium; sodium cyanoborohydride; silver nitrate; acetic acid; pyridinium chlorochromate; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone;

DOI:10.1021/ja00091a004

Reference yield:

Toluene-4-sulfonic acid (2R,3S)-5-hydroxy-2-((Z)-oct-2-enyl)-tetrahydro-furan-3-yl ester (135236-80-5,135236-82-7) → 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)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) HMPA, NaN(SiMe₃)2 / 1.) THF, from -78 deg C to RT, 1.5 h, 2.) THF, from -78 to -30 deg C, 4 h

2: 97 percent / n-Bu₄NF / tetrahydrofuran / 1 h / 24 °C

3: 95 percent / pyridine, AgNO₃ / CH₂Cl₂ / 6 h / Ambient temperature

4: 98 percent / AgNO₃, NBS / acetone / 1 h / 24 °C

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

6: 79 percent / Rieke Zn / tetrahydrofuran; methanol; H₂O / 3 h / Heating

7: 67 percent / 6percent methanolic HCl, NaBH₃CN / ethanol / 3 h / Ambient temperature

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

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

With pyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; aluminum oxide; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tributyltin chloride; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium hexamethyldisilazane; sodium cyanoborohydride; silver nitrate; acetic acid; pyridinium chlorochromate; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone;

DOI:10.1021/ja00091a004

upstream raw materials:

Toluene-4-sulfonic acid (2R,3S)-5-hydroxy-2-((Z)-oct-2-enyl)-tetrahydro-furan-3-yl ester

tert-butylchlorodiphenylsilane

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

(3R,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-3-ol

Downstream raw materials:

(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