Thiopc

Base Information

• Chemical Name: Thiopc
• CAS No.: 146797-82-2
• Molecular Formula: C₄₄H₈₂NO₆PS
• Molecular Weight: 784.178
• Mol file: 146797-82-2.mol

Synonyms:1-hexadecyl-2-arachidonoylthio-2-deoxy-sn-glycero-3-phosphorylcholine;1-hexadecyl-2-arachidonoylthio-2-deoxyglycero-3-phosphorylcholine

Chemical Property of Thiopc

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 120.00000
• Density: g/cm³
• LogP: 13.53640
• XLogP3: 13.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 40
• Exact Mass: 783.56004751
• Heavy Atom Count: 53
• Complexity: 985

Purity/Quality:

99% ^*data from raw suppliers

Arachidonoyl thio-PC ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCCOCC(COP(=O)([O-])OCC[N+](C)(C)C)SC(=O)CCCC=CCC=CCC=CCC=CCCCCC
• Isomeric SMILES: CCCCCCCCCCCCCCCCOC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)SC(=O)CCC/C=C/C/C=C/C/C=C/C/C=C/CCCCC
• Description: Arachidonoyl thio-PC is a substrate for many phospholipase A2s (PLA2s) including sPLA2, cPLA2, and iPLA2. Cleavage of the sn-2 fatty acid by PLA2 results in generation of a free thiol which reacts with chromogenic reagents such as DTNB (Ellman’s reagent) and DTP to allow quantitation of PLA2 activity. Isozyme-specific cPLA2 activity can be measured by excluding or inhibiting sPLA2 and iPLA2 activities in the assay.

Technology Process of Thiopc

There total 19 articles about Thiopc 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:

(S)-2-O-benzyl-3-O-hexadecyl-1-O-tetrahydropyranylglycerol (146923-48-0) → 1-O-hexadecyl-2-thioarachidonyl-2-deoxy-sn-glycero-3-phosphocholine (146797-82-2)

Guidance literature:

Multi-step reaction with 8 steps

1: H₂ / 5percent Pd-C / ethanol

2: 98 percent / pyridine, DMAP

3: 90 percent / acetonitrile

4: LiAlH₄ / tetrahydrofuran

5: diethyl phosphorocyanidate, Et₃N / dimethylformamide

6: PPTS / ethanol / 55 °C

7: Et₃N / CH₂Cl₂

8: 1.) H₂O / 2.) 65 deg C

With pyridine; dmap; lithium aluminium tetrahydride; diethyl cyanophosphonate; water; hydrogen; pyridinium p-toluenesulfonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1248/cpb.39.1335

Reference yield:

(R)-3-(hexadecyloxy)-1,2-propanediol (10550-58-0) → 1-O-hexadecyl-2-thioarachidonyl-2-deoxy-sn-glycero-3-phosphocholine (146797-82-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 85.36 g / Et₃N / tetrahydrofuran; acetonitrile / 15 h / Heating

2: 94.07 g / Et₃N / CH₂Cl₂ / 1.5 h / -5 °C

3: dimethylformamide / 20 h / 90 °C

4: 95 percent / NaOMe / methanol; tetrahydrofuran / 0.5 h / 0 °C

5: 85 percent / BF₃*Et₂O / CH₂Cl₂ / 0.75 h / -10 °C

6: Et₃N / benzene / 3.5 h / Ambient temperature

7: acetonitrile / 16 h / 50 °C

8: 1.) AgNO₃, pyridine, 2.) pyridine, H₂S / 1.) MeOH, CH₃CN, 0 deg C, 30 min, 2.) CH₂Cl₂, 0 deg C, 30 min; room temperature, 1 h

9: 15.8 g / DMAP, DCC / CH₂Cl₂ / 3 h / Ambient temperature

With pyridine; dmap; boron trifluoride diethyl etherate; hydrogen sulfide; sodium methylate; silver nitrate; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1021/jo970882t

Reference yield:

methanesulfonic acid hexadecyl ester (20779-14-0) → 1-O-hexadecyl-2-thioarachidonyl-2-deoxy-sn-glycero-3-phosphocholine (146797-82-2)

Guidance literature:

Multi-step reaction with 11 steps

1: 97 percent / NaH / dimethylformamide / 17 h / Ambient temperature

2: 97 percent / aq.HCl / 1,2-dimethoxy-ethane / 1.5 h / Heating

3: 85.36 g / Et₃N / tetrahydrofuran; acetonitrile / 15 h / Heating

4: 94.07 g / Et₃N / CH₂Cl₂ / 1.5 h / -5 °C

5: dimethylformamide / 20 h / 90 °C

6: 95 percent / NaOMe / methanol; tetrahydrofuran / 0.5 h / 0 °C

7: 85 percent / BF₃*Et₂O / CH₂Cl₂ / 0.75 h / -10 °C

8: Et₃N / benzene / 3.5 h / Ambient temperature

9: acetonitrile / 16 h / 50 °C

10: 1.) AgNO₃, pyridine, 2.) pyridine, H₂S / 1.) MeOH, CH₃CN, 0 deg C, 30 min, 2.) CH₂Cl₂, 0 deg C, 30 min; room temperature, 1 h

11: 15.8 g / DMAP, DCC / CH₂Cl₂ / 3 h / Ambient temperature

With pyridine; hydrogenchloride; dmap; boron trifluoride diethyl etherate; hydrogen sulfide; sodium methylate; sodium hydride; silver nitrate; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1021/jo970882t

upstream raw materials:

trimethylamine

all cis 5,8,11,14-eicosatetraenoic acid

C₂₄H₅₂NO₅PS

(R)-3-(hexadecyloxy)-1,2-propanediol

Refernces

• 1、 Murata,Ikoma,Achiwa. "New synthesis of 2-thio-PAF and related compounds as substrates of PAF acetylhydrolase and phospholipase A2". . p. 1335 - 1336. Retrieved 2007/10/02.