3-O-HEXADECYL-SN-GLYCERO-1-PHOSPHOCHOLINE

Base Information

• Chemical Name: 3-O-HEXADECYL-SN-GLYCERO-1-PHOSPHOCHOLINE
• CAS No.: 90130-75-9
• Molecular Formula: C₂₄H₅₂NO₆P
• Molecular Weight: 481.654
• Mol file: 90130-75-9.mol

Synonyms:ENANTIO-LYSO-PAF (C16);ENANTIO-LYSO-PLATELET ACTIVATING FACTOR (C16);3-O-HEXADECYL-SN-GLYCERO-1-PHOSPHOCHOLINE;3-PALMITYL-SN-GLYCERO-1-PHOSPHOCHOLINE

Chemical Property of 3-O-HEXADECYL-SN-GLYCERO-1-PHOSPHOCHOLINE

Chemical Property:

• PSA: 97.86000
• LogP: 6.12320
• Storage Temp.: -15°C

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-O-HEXADECYL-SN-GLYCERO-1-PHOSPHOCHOLINE

There total 10 articles about 3-O-HEXADECYL-SN-GLYCERO-1-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: 100.0%

3-O-hexadecyl-2-O-benzyl-sn-glycero-1-phosphocholine (96998-53-7) → 3-O-hexadecyl-2-lyso-sn-glycero-1-phosphocholine (90130-75-9,17364-21-5)

Guidance literature:

With hydrogen; palladium dihydroxide; In methanol; water; for 24h;

DOI:10.1021/jo00280a035

Reference yield:

(R)-2-benzyloxy-3-hexadecyloxy-propan-1-ol (84415-90-7) → 3-O-hexadecyl-2-lyso-sn-glycero-1-phosphocholine (90130-75-9,17364-21-5)

Guidance literature:

Multi-step reaction with 2 steps

2: H₂ / Pd/C / ethanol

With hydrogen; palladium on activated charcoal; In ethanol;

Reference yield:

Acetic acid (S)-2-benzyloxy-3-hexadecyloxy-propyl ester → 3-O-hexadecyl-2-lyso-sn-glycero-1-phosphocholine (90130-75-9,17364-21-5)

Guidance literature:

Multi-step reaction with 4 steps

1: LiAlH₄ / diethyl ether / 1.) 0 deg C, 30 min, 2.) RT, 2 h

2: POCl₃, Et₃N / CHCl₃ / 0.5 h / Ambient temperature

3: pyridine / 1.) CHCl₃, RT, 16 h, 2.) 30 min

4: 100 percent / H₂ / 20percent Pd(OH)2/C / methanol; H₂O / 24 h

With pyridine; lithium aluminium tetrahydride; hydrogen; triethylamine; trichlorophosphate; palladium dihydroxide; In methanol; diethyl ether; chloroform; water;

DOI:10.1021/jo00280a035

upstream raw materials:

3-O-hexadecyl-2-O-benzyl-sn-glycero-1-phosphocholine

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

(S)-3-(1-hexadecyloxy)-1-(trityloxy)propan-2-ol

(R)-2-benzyloxy-3-hexadecyloxy-propan-1-ol

Refernces

• 1、 Guivisdalsky, Pedro N.,Bittman, Robert. "An Efficient Stereocontrolled Route to Both Enantiomers of Platelet Activating Factor and Analogues with Long-Chain Esters at C2: Saturated and Unsaturated Ether Glycerolipids by Opening of Glycidyl Arenesulfonates". . p. 4643 - 4648. Retrieved 2007/10/02.