ethyl 5(S)-(benzoyloxy)-12(R)-<(tert-butyldiphenylsilyl)oxy>-6(Z),8(E),10(E),14(Z)-icosatetraenoate

Base Information

• Chemical Name: ethyl 5(S)-(benzoyloxy)-12(R)-<(tert-butyldiphenylsilyl)oxy>-6(Z),8(E),10(E),14(Z)-icosatetraenoate
• CAS No.: 82493-59-2
• Molecular Formula: C₄₅H₅₈O₅Si
• Molecular Weight: 707.038
• Mol file: 82493-59-2.mol

Synonyms:ethyl 5(S)-(benzoyloxy)-12(R)-<(tert-butyldiphenylsilyl)oxy>-6(Z),8(E),10(E),14(Z)-icosatetraenoate

Chemical Property of ethyl 5(S)-(benzoyloxy)-12(R)-<(tert-butyldiphenylsilyl)oxy>-6(Z),8(E),10(E),14(Z)-icosatetraenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 5(S)-(benzoyloxy)-12(R)-<(tert-butyldiphenylsilyl)oxy>-6(Z),8(E),10(E),14(Z)-icosatetraenoate

There total 44 articles about ethyl 5(S)-(benzoyloxy)-12(R)-<(tert-butyldiphenylsilyl)oxy>-6(Z),8(E),10(E),14(Z)-icosatetraenoate 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:

tert-butylchlorodiphenylsilane (58479-61-1) → ethyl 5(S)-(benzoyloxy)-12(R)-<(tert-butyldiphenylsilyl)oxy>-6(Z),8(E),10(E),14(Z)-icosatetraenoate (82493-59-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / dimethylformamide / 22 h / 65 °C

2: 100 percent / aluminum hydride / tetrahydrofuran / 2.5 h / 0 °C

3: 90 percent / CBr₄, ethylenebis(diphenylphosphine) / CH₂Cl₂ / 2.5 h / -35 °C

4: 153 mg / acetonitrile / 1.5 h / 20 °C

5: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, -100 deg C, 2 min, 2.) THF, hexane, from -100 deg C to RT

With aluminium hydride; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; carbon tetrabromide; 1,2-bis-(diphenylphosphino)ethane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo00271a032

Reference yield:

9(R),12(R)-bis<(tert-butyldiphenylsilyl)oxy>-10(S),11(S)-O-(1-methylethylidene)-6,14-icosadiyne-10,11-diol (119414-22-1) → ethyl 5(S)-(benzoyloxy)-12(R)-<(tert-butyldiphenylsilyl)oxy>-6(Z),8(E),10(E),14(Z)-icosatetraenoate (82493-59-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 100 percent / hydrogen / Lindlar catalyst / benzene / Ambient temperature

2: 70 percent / (CH₂SH)2, TsOH / CHCl₃ / 3 h / Heating

3: 55 percent / lead tetraacetate / benzene / 1 h / Ambient temperature

4: 61 percent / benzene / 6 h / Heating

5: 60 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene / acetonitrile / 1 h / 20 °C

6: 100 percent / aluminum hydride / tetrahydrofuran / 2.5 h / 0 °C

7: 90 percent / CBr₄, ethylenebis(diphenylphosphine) / CH₂Cl₂ / 2.5 h / -35 °C

8: 153 mg / acetonitrile / 1.5 h / 20 °C

9: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, -100 deg C, 2 min, 2.) THF, hexane, from -100 deg C to RT

With aluminium hydride; lead(IV) acetate; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; carbon tetrabromide; hydrogen; toluene-4-sulfonic acid; ethane-1,2-dithiol; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,2-bis-(diphenylphosphino)ethane; lithium chloride; Lindlar's catalyst; In tetrahydrofuran; dichloromethane; chloroform; acetonitrile; benzene;

DOI:10.1021/jo00271a032

Reference yield:

1-Heptyne (628-71-7) → ethyl 5(S)-(benzoyloxy)-12(R)-<(tert-butyldiphenylsilyl)oxy>-6(Z),8(E),10(E),14(Z)-icosatetraenoate (82493-59-2)

Guidance literature:

Multi-step reaction with 12 steps

2: 98 percent / hydrogen / Lindlar catalyst / benzene / Ambient temperature

3: 90 percent / 90percent aqueous CF₃COOH / 3 h / 0 °C

4: 65 percent / lead tetraacetate / benzene / 1 h / Ambient temperature

5: 50 percent / benzene / 4 h / Heating

6: NaH / 1.) benzene, RT, 1 h, 2.) benzene, RT, 4 h

7: 80 percent / potassium carbonate / ethanol / 22 h / 45 °C

8: 85 percent / dimethylformamide / 22 h / 65 °C

9: 100 percent / aluminum hydride / tetrahydrofuran / 2.5 h / 0 °C

10: 90 percent / CBr₄, ethylenebis(diphenylphosphine) / CH₂Cl₂ / 2.5 h / -35 °C

11: 153 mg / acetonitrile / 1.5 h / 20 °C

12: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, -100 deg C, 2 min, 2.) THF, hexane, from -100 deg C to RT

With aluminium hydride; lead(IV) acetate; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; carbon tetrabromide; hydrogen; sodium hydride; potassium carbonate; trifluoroacetic acid; 1,2-bis-(diphenylphosphino)ethane; Lindlar's catalyst; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1021/jo00271a032

upstream raw materials:

ethyl 2-O benzoyl-3,4,5-trideoxy-L-glycero-hexuronate

<6(R)-<(tert-butyldiphenylsilyl)oxy>-2(E),4(E),8(Z)-tetradecatrien-1-yl>triphenylphosphonium bromide

(R)-ethyl-5-benzoyloxy-5-formyl pentanoate

1-Heptyne

Downstream raw materials:

12-epi-leukotriene B4

(5S,12R,6Z,8E,10E,14Z)-ethyl 5-benzoyloxy-12-hydroxyicosatetra-6,8,10,14-enoate

Leukotriene B

Refernces

• 1、 Le Merrer,Gravier,Languin-Micas,Depezay. "Total synthesis of leukotriene (+)-LTB4 from D-mannitol". . p. 4161 - 4164. Retrieved 2007/10/02.