12(R),15(R)-dibenzoyloxy-6(Z),9(Z),17(Z),20(Z)-hexaeicosatetraene-13(S),14(S) diol

Base Information

• Chemical Name: 12(R),15(R)-dibenzoyloxy-6(Z),9(Z),17(Z),20(Z)-hexaeicosatetraene-13(S),14(S) diol
• CAS No.: 129414-15-9
• Molecular Formula: C₄₀H₅₄O₆
• Molecular Weight: 630.865
• Mol file: 129414-15-9.mol

Synonyms:

Chemical Property of 12(R),15(R)-dibenzoyloxy-6(Z),9(Z),17(Z),20(Z)-hexaeicosatetraene-13(S),14(S) diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 12(R),15(R)-dibenzoyloxy-6(Z),9(Z),17(Z),20(Z)-hexaeicosatetraene-13(S),14(S) diol

There total 19 articles about 12(R),15(R)-dibenzoyloxy-6(Z),9(Z),17(Z),20(Z)-hexaeicosatetraene-13(S),14(S) diol 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%

12(S),15(S)-dibenzoyloxy-13(R),14(R)-O-methylethylidene-6(Z),9(Z),17(Z),20(Z)-hexaeicosatetraene-13,14-diol (121525-73-3,121570-62-5) → 12(S),15(S)-dibenzoyloxy-6(Z),9(Z),17(Z),20(Z)-hexaeicosatetraene-13,14-diol (129414-15-9,129446-74-8)

Guidance literature:

With trifluoroacetic acid; at -5 ℃; for 0.5h;

DOI:10.1016/S0040-4020(01)89193-6

Reference yield: 100.0%

12(R),15(R)-dibenzoyloxy-13(R),14(R)-O-methylethylidene-6(Z),9(Z),17(Z),20(Z)-hexaeicosatetraene-13,14-diol (121525-73-3,121570-62-5) → 12(R),15(R)-dibenzoyloxy-6(Z),9(Z),17(Z),20(Z)-hexaeicosatetraene-13(S),14(S) diol (129414-15-9,129446-74-8)

Guidance literature:

With trifluoroacetic acid; In water; at -5 ℃; for 0.5h;

Reference yield:

1,2:5,6-dianhydro-3,4-O-methylethylidene-L-iditol (63699-97-8) → 12(S),15(S)-dibenzoyloxy-6(Z),9(Z),17(Z),20(Z)-hexaeicosatetraene-13,14-diol (129414-15-9,129446-74-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) HMPA / 1) THF, 20h, reflux, 2) 0 deg C

2: 70 percent / Ph₂PC₂H₄PPh₂, Br₂ / CH₂Cl₂ / 1.5 h / 25 °C

4: 60 percent / H₂, 1percent quinoline / 5percent Pd/BaSO₄ / ethyl acetate

5: 100 percent / CF₃COOH / H₂O / 0.5 h / -5 °C

With quinoline; N,N,N,N,N,N-hexamethylphosphoric triamide; hydrogen; bromine; trifluoroacetic acid; 1,2-bis-(diphenylphosphino)ethane; Pd-BaSO₄; In dichloromethane; water; ethyl acetate;

upstream raw materials:

12(S),15(S)-dibenzoyloxy-13(R),14(R)-O-methylethylidene-6(Z),9(Z),17(Z),20(Z)-hexaeicosatetraene-13,14-diol

1-Heptyne

benzoyl chloride

5(S),8(S)-dibenzoyloxy-1,12-dibromo-6(R),7(R)-O-methylethylidene-2,10-dodecadiyn-6,7-diol

Downstream raw materials:

methyl 9(R)-benzoyloxy-5(Z),7(E),11(Z),14(Z)-eicosatetraenoate

9(R)-benzoyloxy-5(Z),7(E),11(Z),14(Z)-eicosatetraenoic acid

4(R)-benzoyloxy-2(E),6(Z),9(Z)-pentadecatrienal

2(R)-benzoyloxy-4(Z),7(Z)-tridecadienal