methyl 5(S)-(benzoyloxy)-12(R)-hydroxy-6(Z),8(E),10(E),14(Z)-eicosatetraenoate

Base Information

• Chemical Name: methyl 5(S)-(benzoyloxy)-12(R)-hydroxy-6(Z),8(E),10(E),14(Z)-eicosatetraenoate
• CAS No.: 76745-31-8
• Molecular Formula: C₂₈H₃₈O₅
• Molecular Weight: 454.607
• Mol file: 76745-31-8.mol

Synonyms:methyl 5(S)-(benzoyloxy)-12(R)-hydroxy-6(Z),8(E),10(E),14(Z)-eicosatetraenoate

Chemical Property of methyl 5(S)-(benzoyloxy)-12(R)-hydroxy-6(Z),8(E),10(E),14(Z)-eicosatetraenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 5(S)-(benzoyloxy)-12(R)-hydroxy-6(Z),8(E),10(E),14(Z)-eicosatetraenoate

There total 37 articles about methyl 5(S)-(benzoyloxy)-12(R)-hydroxy-6(Z),8(E),10(E),14(Z)-eicosatetraenoate 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: 48.0%

methyl 5(S)-(benzoyloxy)-12(R)-(tert-butyldiphenylsiloxy)-6(Z),8(E),10(E),14(Z)-eicosatetraenoate (101226-20-4) → methyl 5(S)-(benzoyloxy)-12(R)-hydroxy-6(Z),8(E),10(E),14(Z)-eicosatetraenoate (76745-31-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 5h;

DOI:10.1021/jo00358a016

Reference yield: 32.0%

Methyl 5S-benzoyloxy-5-formylvalerate (76745-20-5) + ((2E,4E,8Z)-(R)-6-Hydroxy-tetradeca-2,4,8-trienyl)-triphenyl-phosphonium; bromide (76745-29-4) → methyl 5(S)-(benzoyloxy)-12(R)-hydroxy-6(Z),8(E),10(E),14(Z)-eicosatetraenoate (76745-31-8)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; In tetrahydrofuran; 1.) -78 deg C, 30 min, 2.) -78 deg C -> -20 deg C, 30 min, 3.) -20 deg C -> 0 deg C, 30 min;

DOI:10.1021/ja00547a051

Reference yield:

hexylidenetriphenylphosphoran (16666-79-8,19493-12-0) → methyl 5(S)-(benzoyloxy)-12(R)-hydroxy-6(Z),8(E),10(E),14(Z)-eicosatetraenoate (76745-31-8)

Guidance literature:

Multi-step reaction with 10 steps

1: 70 percent / hexamethylphosphoric triamide / tetrahydrofuran / 1.) -78 deg C, 0.5 h, 2.) -78 deg C to -20 deg C, 3 h, 3.) -20 deg C, 72 h

2: 97 percent / pyridine / 96 h / 23 °C

3: 10percent methanolic HCl / 8 h / 23 °C

4: 1.) pyridine, 2.) diazabicyclo<4.3.0>nonene / 1.) methylene chloride, 0 deg C, 1 h, 2.) THF, 75 deg C, 9 h

5: 95 percent / lithium hydroxide / 1,2-dimethoxy-ethane; H₂O / 2 h / 23 °C

6: 95 percent / lead tetraacetate / CH₂Cl₂ / 0.5 h / -45 °C

7: 70 percent / tetrahydrofuran / 0.5 h / -40 deg C -> -10 deg C

8: hydrogen bromide / CH₂Cl₂ / 0.5 h / 23 °C

9: CH₂Cl₂ / 18 h / 23 °C

10: 32 percent / n-butyllithium, HMPA / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) -78 deg C -> -20 deg C, 30 min, 3.) -20 deg C -> 0 deg C, 30 min

With pyridine; lead(IV) acetate; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hydroxide; n-butyllithium; diazabicyclo<4.3.0>nonene; hydrogen bromide; In tetrahydrofuran; pyridine; 1,2-dimethoxyethane; dichloromethane; water;

DOI:10.1021/ja00547a051

upstream raw materials:

Methyl 5S-benzoyloxy-5-formylvalerate

((2E,4E,8Z)-(R)-6-Hydroxy-tetradeca-2,4,8-trienyl)-triphenyl-phosphonium; bromide

methyl 5(S)-(benzoyloxy)-12(R)-(tert-butyldiphenylsiloxy)-6(Z),8(E),10(E),14(Z)-eicosatetraenoate

Pentanedioic acid, monomethyl ester

Downstream raw materials:

Leukotriene B

6-trans-Leukotriene B₄

Refernces

• 1、 Corey,Marfat,Goto,Brion. "Leukotriene B. Total synthesis and assignment of stereochemistry". . p. 7984 - 7985. Retrieved 2007/10/02.