Hexadecanoic acid, (1R)-1-bis(1-methylethyl)amino(phenylmethoxy)phosphinooxymethyl-1,2-ethanediyl ester

Base Information

• Chemical Name: Hexadecanoic acid, (1R)-1-bis(1-methylethyl)amino(phenylmethoxy)phosphinooxymethyl-1,2-ethanediyl ester
• CAS No.: 120595-85-9
• Molecular Formula: C48H88 N O6 P
• Molecular Weight: 806.204
• DSSTox Substance ID: DTXSID101111241
• Nikkaji Number: J971.576B
• Mol file: 120595-85-9.mol

Synonyms:Hexadecanoicacid, (1R)-1-[[[[bis(1-methylethyl)amino](phenylmethoxy)phosphino]oxy]methyl]-1,2-ethanediylester (9CI); Hexadecanoic acid,1-[[[[bis(1-methylethyl)amino](phenylmethoxy)phosphino]oxy]methyl]-1,2-ethanediylester, (1R)-

Chemical Property of Hexadecanoic acid, (1R)-1-bis(1-methylethyl)amino(phenylmethoxy)phosphinooxymethyl-1,2-ethanediyl ester

Chemical Property:

• PSA: 87.89000
• LogP: 14.98310
• XLogP3: 17.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 42
• Exact Mass: 805.63492652
• Heavy Atom Count: 56
• Complexity: 874

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OCC(COP(N(C(C)C)C(C)C)OCC1=CC=CC=C1)OC(=O)CCCCCCCCCCCCCCC
• Isomeric SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(N(C(C)C)C(C)C)OCC1=CC=CC=C1)OC(=O)CCCCCCCCCCCCCCC

Technology Process of Hexadecanoic acid, (1R)-1-bis(1-methylethyl)amino(phenylmethoxy)phosphinooxymethyl-1,2-ethanediyl ester

There total 15 articles about Hexadecanoic acid, (1R)-1-bis(1-methylethyl)amino(phenylmethoxy)phosphinooxymethyl-1,2-ethanediyl ester 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: 97.0%

1,2-dipalmitoyl-sn-glycerol (30334-71-5) + benzyl-N,N,N',N'-tetraisopropylphosphorodiamidite (108549-21-9) → (+)-benzyloxy(N,N-diisopropylamino)(1,2-di-O-hexadecanoyl-sn-glycer-3-yl)phosphine (120595-85-9,196304-47-9)

Guidance literature:

With 1H-tetrazole; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1039/b909306k

Reference yield: 92.0%

1,2-di-O-palmitoyl-sn-glycerol (6076-30-8) + benzyl-N,N,N',N'-tetraisopropylphosphorodiamidite (108549-21-9) → 1,2-di-O-hexadacanoyl-sn-glycerobenzyl (N,N-diisopropylamino)phopshoramidite (120595-85-9,196304-47-9)

Guidance literature:

With 1H-tetrazole; In dichloromethane; acetonitrile; at 20 ℃; for 0.5h;

DOI:10.1016/S0040-4039(00)82387-4

Reference yield: 90.0%

1,2-di-O-palmitoyl-sn-glycerol (6076-30-8) + (benzyloxy)chloro(diisopropylamino)phosphane (128753-68-4) → 1,2-di-O-hexadacanoyl-sn-glycerobenzyl (N,N-diisopropylamino)phopshoramidite (120595-85-9,196304-47-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1021/jo980501r

upstream raw materials:

1,2-di-O-palmitoyl-sn-glycerol

benzyl-N,N,N',N'-tetraisopropylphosphorodiamidite

(benzyloxy)chloro(diisopropylamino)phosphane

bis(diisopropylamino)chlorophosphine

Downstream raw materials:

3,4,5-tri-O-benzyl-2,6-di-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-1-O-(1,2-di-O-hexadecanoyl-sn-glycero-3-O-benzylphosphono)-D-myo-inositol

3,4,5,6-tetra-O-benzyl-1-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-2-O-[((R)-2,3-dipalmitoyloxypropyl)-(benzyl)phosphoryl]-D-myo-inositol

dipalmitoyl PtdIns₄P

(-)-1-O-(1,2-di-O-palmitoyl-sn-glycerol-3-benzyloxyphosphoryl)-2,6-di-O-benzyl-myo-inositol 3,4,5-tris(dibenzyl phosphate)