(2r)-3-(Hexadecyloxy)-2-methoxypropyl 2-(trimethylammonio)ethyl phosphate

Base Information

• Chemical Name: (2r)-3-(Hexadecyloxy)-2-methoxypropyl 2-(trimethylammonio)ethyl phosphate
• CAS No.: 78858-44-3
• Molecular Formula: C₂₅H₅₄NO₆P
• Molecular Weight: 495.681
• DSSTox Substance ID: DTXSID701000084
• ChEMBL ID: CHEMBL313574
• Mol file: 78858-44-3.mol

Synonyms:1-hexadecyl-2-methoxyglycero-3-phosphocholine;1-O-hexadecyl-2-O-methyl-rac-glycero-3-phosphocholine;1-O-hexadecyl-2-O-methylglycero-3-phosphocholine;AMG-PC;ET-16-OCH3;ET16-OMe;HD-MO-GPC;rac-1-hexadecyl 2-methyl phosphatidylcholine

Chemical Property of (2r)-3-(Hexadecyloxy)-2-methoxypropyl 2-(trimethylammonio)ethyl phosphate

Chemical Property:

• PSA: 86.86000
• LogP: 6.77730
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 25
• Exact Mass: 495.36887544
• Heavy Atom Count: 33
• Complexity: 464

Purity/Quality:

98%min ^*data from raw suppliers

2-O-methyl PAF C-16 ≥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)OC
• Isomeric SMILES: CCCCCCCCCCCCCCCCOC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)OC
• Description: 2-O-methyl PAF C-16 is a synthetic PAF analog which contains a methyl group, attached by an ether linkage, at the sn-2 position. Although the biological activities of 2-O-methyl PAF C-16 have not been well characterized, the C-18 analog has been shown to mediate a number of biological responses including decreasing plasma membrane fluidity and inhibiting tumor cell invasiveness in embryonic chick heart. In rat astrocytes, the C-18 analog causes the release of large quantities of NO by a pathway involving activation of NOS.

Technology Process of (2r)-3-(Hexadecyloxy)-2-methoxypropyl 2-(trimethylammonio)ethyl phosphate

There total 16 articles about (2r)-3-(Hexadecyloxy)-2-methoxypropyl 2-(trimethylammonio)ethyl phosphate 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:

1-O-hexadecyl-2-O-methyl-sn-glycerol (96960-92-8,111188-59-1) → 1-O-hexadecyl-2-O-methyl-sn-glycero(3)phosphocholine (78858-44-3)

Guidance literature:

Multi-step reaction with 3 steps

1: diisopropylethylamine / CH₂Cl₂ / 0.67 h / -20 °C

2: Br₂ / CH₂Cl₂ / -20 --> 0 deg C, then 0 deg C, 10 min

3: propan-2-ol; acetonitrile; CHCl₃; H₂O

With bromine; N-ethyl-N,N-diisopropylamine; In dichloromethane; chloroform; water; isopropyl alcohol; acetonitrile;

DOI:10.1016/S0040-4039(00)78183-4

Reference yield:

methanesulfonic acid hexadecyl ester (20779-14-0) → 1-O-hexadecyl-2-O-methyl-sn-glycero(3)phosphocholine (78858-44-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 88 percent / KH (22percent) / benzene / 2 h / Heating

2: 87 percent / H₂ / palladium black / methanol; acetic acid / 760 Torr / Ambient temperature

3: 1.) KH / 1.) benzene, room temp.; 2.) room temp., 2 h

4: 98 percent / HCl (6N) / tetrahydrofuran / 0.08 h / Ambient temperature

5: 1.) Pb(OAc)4; 2.) NaBH₄ / 1.) benzene, room temp.; 2.) MeOH, THF, room temp.

6: 2.) AgOAc / 1.) methanol, 55 deg C, overnight; 2.) 90 percent aqueous methanol, 2 h

With lead(IV) acetate; hydrogenchloride; sodium tetrahydroborate; hydrogen; silver(I) acetate; potassium hydride; palladium; In tetrahydrofuran; methanol; acetic acid; benzene;

DOI:10.1248/cpb.33.572

Reference yield:

1-Hexadecanol (36653-82-4,124-29-8) → 1-O-hexadecyl-2-O-methyl-sn-glycero(3)phosphocholine (78858-44-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / BF₃ etherate / CHCl₃ / 24 h

2: 90 percent / 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 16 h / Heating

3: 81 percent / potassium superoxide / 18-crown-6 / dimethylsulfoxide; dimethylformamide; 1,2-dimethoxy-ethane / 6 h / Ambient temperature

4: 100 percent / triethylamine / benzene / 2 h / Ambient temperature

5: acetonitrile / 36 h / 65 - 70 °C

With potassium superoxide; 2,6-di-tert-butyl-4-methylpyridine; boron trifluoride diethyl etherate; triethylamine; 18-crown-6 ether; In 1,2-dimethoxyethane; dichloromethane; chloroform; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1021/jo00280a034

upstream raw materials:

2-bromoethylphosphoric acid dichloride

1-O-hexadecyl-2-O-methyl-sn-glycerol

trimethylamine

2-(1-hexadecyl-2-methyl-sn-glycerol)-2-oxo-1,3,2-dioxaphospholane

Refernces

• 1、 Guivisdalsky, Pedro N.,Bittman, Robert. "Regiospecific Opening of Glycidyl Derivatives Mediated by Boron Trifluoride. Asymmetric Synthesis of Ether-Linked Phospholipids". . p. 4637 - 4642. Retrieved 2007/10/02.
• 2、 Bhatia, Suresh K.,Hajdu, Joseph. "A NEW APPROACH TO THE SYNTHESIS OF ETHER PHOSPHOLIPIDS. PREPARATION OF 1,2-DIALKYLGLYCEROPHOSPHORYLCHOLINES FROM L-GLYCERIC ACID". . p. 271 - 274. Retrieved 2007/10/02.