tetracosanoic acid N-hydroxysuccinimide ester

Base Information

• Chemical Name: tetracosanoic acid N-hydroxysuccinimide ester
• CAS No.: 39782-75-7
• Molecular Formula: C₂₈H₅₁NO₄
• Molecular Weight: 465.717
• Mol file: 39782-75-7.mol

Synonyms:

Chemical Property of tetracosanoic acid N-hydroxysuccinimide ester

Chemical Property:

• Boiling Point: 546.0±33.0 °C(Predicted)
• Density: 0.98±0.1 g/cm3(Predicted)

Purity/Quality:

>95.00% ^*data from raw suppliers

1-[(1-Oxotetracosyl)oxy]-2,5-pyrrolidinedione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 1-[(1-Oxotetracosyl)oxy]-2,5-pyrrolidinedione is an intermediate in synthesizing C24 Ceramide (C263450). Production of ceramide occurs upon hydrolysis of sphingomyelin by a specific isoform of phospholipase C, appropriately named sphingomyelinase.

Technology Process of tetracosanoic acid N-hydroxysuccinimide ester

There total 1 articles about tetracosanoic acid N-hydroxysuccinimide 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: 99.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + n-tetracosanoic acid (557-59-5) → tetracosanoic acid N-hydroxysuccinimide ester (39782-75-7)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1021/ja8026373

Reference yield:

tetracosanoic acid N-hydroxysuccinimide ester (39782-75-7) → (2S,3R,4E)-2-tetracosanamido-1-O-trityl-hexadec-4-ene-1,3-diol

Guidance literature:

Multi-step reaction with 2 steps

1.1: trifluoroacetic acid / water; dichloromethane / 1.5 h / 20 °C / Inert atmosphere

1.2: 2 h / 20 °C / Inert atmosphere

1.3: 2 h / 20 °C / Inert atmosphere

2.1: dmap; pyridine / 11 h / 50 °C / Inert atmosphere

With pyridine; dmap; trifluoroacetic acid; In dichloromethane; water;

DOI:10.1021/acs.orglett.9b01229

Reference yield:

tetracosanoic acid N-hydroxysuccinimide ester (39782-75-7) → Benzyl 3-O-(D-1-carboxyethyl)-2-deoxy-4,6-O-isopropylidene-2-(tetracosanoylamino)-α-D-glucopyranoside (81639-19-2)

Guidance literature:

Multi-step reaction with 2 steps

1: dioxane / 5 h / Ambient temperature

2: 84 percent / sodium hydride / dioxane / 1.) 90 deg C, 1 h, 2.) 60 deg, 5 h

With sodium hydride; In 1,4-dioxane;

DOI:10.1271/bbb1961.46.507

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

n-tetracosanoic acid

Downstream raw materials:

Benzyl 2-deoxy-4,6-O-isopropylidene-2-(tetracosanoylamino)-α-D-glucopyranoside

Benzyl 3-O-(D-1-carboxyethyl)-2-deoxy-4,6-O-isopropylidene-2-(tetracosanoylamino)-α-D-glucopyranoside

Refernces

• 1、 Okumura,Kamisango,Saiki,et al.. "Synthesis and immunoadjuvant activity of acylamino analogs of N-acetylmuramoyl-L-alanyl-D-isoglutamine". . p. 507 - 514. Retrieved 2007/10/02.