1-palmitoyl-2-(21-diphenylhexatrienyl-henicosanoyl)-sn-glycero-3-phosphocholine

Base Information

• Chemical Name: 1-palmitoyl-2-(21-diphenylhexatrienyl-henicosanoyl)-sn-glycero-3-phosphocholine
• CAS No.: 128368-78-5
• Molecular Formula: C₆₃H₁₀₄NO₈P
• Molecular Weight: 1034.49
• Mol file: 128368-78-5.mol

Synonyms:

Chemical Property of 1-palmitoyl-2-(21-diphenylhexatrienyl-henicosanoyl)-sn-glycero-3-phosphocholine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-palmitoyl-2-(21-diphenylhexatrienyl-henicosanoyl)-sn-glycero-3-phosphocholine

There total 23 articles about 1-palmitoyl-2-(21-diphenylhexatrienyl-henicosanoyl)-sn-glycero-3-phosphocholine 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: 8.0%

1-palmitoyl-sn-glycero-3-phosphocholine (17364-16-8,17364-17-9,17364-18-0,14863-27-5) + 1-Imidazol-1-yl-21-[4-((1E,3E,5E)-6-phenyl-hexa-1,3,5-trienyl)-phenyl]-henicosan-1-one → 1-palmitoyl-2-(21-diphenylhexatrienyl-henicosanoyl)-sn-glycero-3-phosphocholine (128368-78-5)

Guidance literature:

In chloroform; at 50 ℃; for 120h;

DOI:10.1039/c39900000031

Reference yield:

1,20-eicosanediol (7735-43-5) → 1-palmitoyl-2-(21-diphenylhexatrienyl-henicosanoyl)-sn-glycero-3-phosphocholine (128368-78-5)

Guidance literature:

Multi-step reaction with 13 steps

1: 49 percent / 48percent aq. HBr / petroleum ether / 24 h / Heating

2: PPTS / CH₂Cl₂ / 20 h / Ambient temperature

3: 1) lithium diisopropylamide / 1) THF, 0 deg C, 30 min, 2) THF, 30 min

4: 67 percent / BH₃-Me₂S / tetrahydrofuran / 20 h / Ambient temperature

5: 85 percent / 4-(dimethylamino)pyridine, pyridine / CH₂Cl₂ / 20 h / Ambient temperature

6: 95 percent / PPTS / ethanol / 1 h / Heating

7: 87 percent / Jones reagent / acetone

8: 78 percent / diethyl ether; tetrahydrofuran / 0 °C

9: 69 percent / K₂CO₃ / methanol; tetrahydrofuran / 0.75 h / Ambient temperature

10: 76 percent / CrO₃, pyridine / CH₂Cl₂ / 0.25 h / Ambient temperature

11: 66 percent / NaOCH₃ / tetrahydrofuran / 0.5 h / 0 °C

12: 82 percent / KOH / toluene; methanol / 20 h / Heating

13: 1) 1,1'-thionyldiimidazole / 1) THF, 1 h, 2)CHCl₃, 5 days, room temperature

With pyridine; chromium(VI) oxide; dmap; potassium hydroxide; jones reagent; dimethylsulfide borane complex; hydrogen bromide; sodium methylate; pyridinium p-toluenesulfonate; potassium carbonate; N,N'-Thionyldiimidazole; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; acetone; toluene; Petroleum ether;

DOI:10.1016/S0040-4020(01)86422-X

Reference yield:

(2E, 4E)-5-phenylpenta-2,4-dienal (13466-40-5) → 1-palmitoyl-2-(21-diphenylhexatrienyl-henicosanoyl)-sn-glycero-3-phosphocholine (128368-78-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 97 percent / DIBAH / tetrahydrofuran / 2 h / Ambient temperature

2: PCl₃ / diethyl ether / 1) 0 deg C, 15 min, 2) room temperature, 10 h

3: 7 h / 130 °C

4: 66 percent / NaOCH₃ / tetrahydrofuran / 0.5 h / 0 °C

5: 82 percent / KOH / toluene; methanol / 20 h / Heating

6: 1) 1,1'-thionyldiimidazole / 1) THF, 1 h, 2)CHCl₃, 5 days, room temperature

With potassium hydroxide; sodium methylate; diisobutylaluminium hydride; N,N'-Thionyldiimidazole; phosphorus trichloride; In tetrahydrofuran; methanol; diethyl ether; toluene;

DOI:10.1016/S0040-4020(01)86422-X

upstream raw materials:

1-palmitoyl-sn-glycero-3-phosphocholine

21-[4-((1E,3E,5E)-6-Phenyl-hexa-1,3,5-trienyl)-phenyl]-henicosanoic acid

1,20-eicosanediol

(2E, 4E)-5-phenylpenta-2,4-dienal

Refernces

• 1、 Beck,Heissler,Duportail. "1,1'-Thionyldi-imidazole in the synthesis of a long-chain phospholipidic membrane probe". . p. 31 - 32. Retrieved 2007/10/02.