[(2S)-2-hexadecanoyloxy-3-phenylmethoxypropyl] hexadecanoate

Base Information

• Chemical Name: [(2S)-2-hexadecanoyloxy-3-phenylmethoxypropyl] hexadecanoate
• CAS No.: 30403-51-1
• Molecular Formula: C10H12Ce12O5
• Molecular Weight: 659.047
• DSSTox Substance ID: DTXSID701160115
• Nikkaji Number: J72.456D
• Mol file: 30403-51-1.mol

Synonyms:30403-51-1;[(2S)-2-hexadecanoyloxy-3-phenylmethoxypropyl] hexadecanoate;1,2-Dipalmitoyl-3-O-benzyl-sn-glycerol;SCHEMBL1092063;DTXSID701160115;1,2-dipalmitoyl-3-benzyl-sn-glycerol;[S,(+)]-3-O-Benzyl-1-O,2-O-dipalmitoyl-L-glycerol;1,1'-[(1S)-1-[(Phenylmethoxy)methyl]-1,2-ethanediyl] dihexadecanoate

Chemical Property of [(2S)-2-hexadecanoyloxy-3-phenylmethoxypropyl] hexadecanoate

Chemical Property:

• Melting Point: 62.8-64.6 °C(Solv: hexane (110-54-3))
• Boiling Point: 691.2±45.0 °C(Predicted)
• PSA: 61.83000
• Density: 0.945±0.06 g/cm3(Predicted)
• LogP: 12.62080
• XLogP3: 16.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 37
• Exact Mass: 658.55362546
• Heavy Atom Count: 47
• Complexity: 674

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OCC(COCC1=CC=CC=C1)OC(=O)CCCCCCCCCCCCCCC
• Isomeric SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@H](COCC1=CC=CC=C1)OC(=O)CCCCCCCCCCCCCCC

Technology Process of [(2S)-2-hexadecanoyloxy-3-phenylmethoxypropyl] hexadecanoate

There total 17 articles about [(2S)-2-hexadecanoyloxy-3-phenylmethoxypropyl] hexadecanoate 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: 98.0%

(R)-3-benzyloxy-1,2-propanediol (56552-80-8) + 1-hexadecylcarboxylic acid (57-10-3) → 1,2-di-O-hexacecanoyl-3-O-benzyl-sn-glycerol (30403-51-1)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 10h; Ambient temperature;

DOI:10.1021/jo00096a023

Reference yield: 84.0%

(R)-3-benzyloxy-1,2-propanediol (56552-80-8) + n-hexadecanoyl chloride (112-67-4) → 1,2-di-O-hexacecanoyl-3-O-benzyl-sn-glycerol (30403-51-1)

Guidance literature:

With pyridine; In benzene; at 60 - 70 ℃; for 24h;

DOI:10.1021/jm00117a020

Reference yield: 84.0%

1-hexadecylcarboxylic acid (57-10-3) + 1-O-hexadecanoyl-3-O-benzyl-sn-glycerol (1487-50-9) → 1,2-di-O-hexacecanoyl-3-O-benzyl-sn-glycerol (30403-51-1)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1021/acs.orglett.0c00487

upstream raw materials:

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

n-hexadecanoyl chloride

1-hexadecylcarboxylic acid

1-O-hexadecanoyl-3-O-benzyl-sn-glycerol

Downstream raw materials:

L-dipalmitoylphosphatidylcholine

1,2-dipalmitoyl-sn-glycero-3-phosphatidic acid

C₄₄H₇₉N₃O₁₅P₂^(2-)*2Na⁽¹⁺⁾

1,2-di-O-hexadecanoyl-sn-glycerol 3-(2-benzyloxycarbonylaminoethyl)phosphonate

Refernces

• 1、 Ghotekar, Balasaheb K.,Kulkarni, Suvarn S.,Podilapu, Ananda Rao. "Total Synthesis of the Lipid-Anchor-Attached Core Trisaccharides of Lipoteichoic Acids of Streptococcus pneumoniae and Streptococcus oralis Uo5". supporting information. . Retrieved 2020/02/04.
• 2、 Nishida, Yoshihiro,Yuan, Mengfei,Fukuda, Kazuo,Fujisawa, Kaito,Dohi, Hirofumi,Uzawa, Hirotaka. "Remarkable functions of sn-3 hydroxy and phosphocholine groups in 1,2-diacyl-sn-glycerolipids to induce clockwise (+)-helicity around the 1,2-diacyl moiety: Evidence from conformation analysis by 1H NMR spectroscopy". supporting information. p. 1999 - 2009. Retrieved 2017/10/16.