Hexacosanoic acid, 4-nitrophenyl ester

Base Information

• Chemical Name: Hexacosanoic acid, 4-nitrophenyl ester
• CAS No.: 205371-71-7
• Molecular Formula: C32H55NO4
• Molecular Weight: 517.793
• DSSTox Substance ID: DTXSID40447894
• Wikidata: Q82266794
• Mol file: 205371-71-7.mol

Synonyms:Hexacosanoic acid, 4-nitrophenyl ester;205371-71-7;SCHEMBL1170899;DTXSID40447894

Chemical Property of Hexacosanoic acid, 4-nitrophenyl ester

Chemical Property:

• XLogP3: 14.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 26
• Exact Mass: 517.41310924
• Heavy Atom Count: 37
• Complexity: 525

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)OC1=CC=C(C=C1)[N+](=O)[O-]

Technology Process of Hexacosanoic acid, 4-nitrophenyl ester

There total 2 articles about Hexacosanoic acid, 4-nitrophenyl 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: 83.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + 1-hexacosanoic acid (506-46-7) → cerotic acid para-nitrophenyl ester (205371-71-7)

Guidance literature:

With dicyclohexyl-carbodiimide; dmap; In dichloromethane; at 20 ℃; for 16h; In the dark;

Reference yield:

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + hexacosanoyl chloride (145411-41-2) → cerotic acid para-nitrophenyl ester (205371-71-7)

Guidance literature:

With dmap; In tetrahydrofuran; pyridine; at -5 ℃; for 1h; Inert atmosphere;

DOI:10.3390/molecules190710090

Reference yield: 84.0%

cerotic acid para-nitrophenyl ester (205371-71-7) + [(E)-(S)-1-((4S,5R)-2,2-Dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-3-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-allyl]-carbamic acid tert-butyl ester (799268-03-4) → C79H123NO8 (865880-62-2)

Guidance literature:

[(E)-(S)-1-((4S,5R)-2,2-Dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-3-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-allyl]-carbamic acid tert-butyl ester; With triethylsilane; trifluoroacetic acid; In dichloromethane; at 0 ℃; for 2h;

cerotic acid para-nitrophenyl ester; With dmap; In tetrahydrofuran; Product distribution / selectivity;

upstream raw materials:

4-nitro-phenol

1-hexacosanoic acid

hexacosanoyl chloride

Downstream raw materials:

(2S,3R)-3-O-benzyl-2-(N-hexacosanoylamino)octadecan-1,3-diol

(2S,3R)-3-benzyloxy-2-(N-hexacosanoylamino)-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)octadecane

(2S,3R,6R,7S)-2,7-(di-N-hexacosanoylamino)-3,6-dihydroxy-1,8-di(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)oct-4-ene

C₇₉H₁₂₃NO₈

Refernces

• 1、 -. "ALPHA-GALACTOSYLCERAMIDE ANALOGS, THEIR METHODS OF MANUFACTURE, INTERMEDIATE COMPOUNDS USEFUL IN THESE METHODS, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM". Page/Page column 51-52. . Retrieved 2008/12/05.