N-stearoyl cerebroside

Base Information

• Chemical Name: N-stearoyl cerebroside
• CAS No.: 36271-49-5
• Molecular Formula: C₄₂H₈₁NO₈
• Molecular Weight: 728.107
• Mol file: 36271-49-5.mol

Synonyms:Octadecanamide,N-[(1S,2R,3E)-1-[(b-D-galactopyranosyloxy)methyl]-2-hydroxy-3-heptadecenyl]- (9CI);Octadecanamide, N-[1-[(b-D-galactopyranosyloxy)methyl]-2-hydroxy-3-heptadecenyl]-,[R-[R*,S*-(E)]]-; C18-Cerebroside

Chemical Property of N-stearoyl cerebroside

Chemical Property:

• Refractive Index: 1.516
• PSA: 148.71000
• LogP: 8.55830
• Storage Temp.: Refrigerator
• Solubility.: Chloroform : Methanol = 1 : 1

Purity/Quality:

97% ^*data from raw suppliers

β-Galactosyl-C18-ceramide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Galactosylceramides play an important roles in promoting the regulation of nerve cells, regulating protein kinase C activities and modulating the function of the hormone receptor. They have shown to have significant immunostimulatory and anti-umor activity in mice with liver metastasis of the Colon26 adenocarcinoma.

Technology Process of N-stearoyl cerebroside

There total 15 articles about N-stearoyl cerebroside 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: 79.0%

C70H97NO12 (1200446-80-5) → (2S,3R,4E)-1-(β-D-galactopyranosyloxy)-2-(octadecanoylamino)-3-hydroxyoctadec-4-ene (36271-49-5)

Guidance literature:

With sodium methylate; In methanol; dichloromethane;

DOI:10.1021/ol403688t

Reference yield: 71.0%

psychosine (2238-90-6,52050-17-6,56453-02-2,95119-84-9,95975-32-9,106565-70-2) + Stearoyl chloride (112-76-5) → (2S,3R,4E)-1-(β-D-galactopyranosyloxy)-2-(octadecanoylamino)-3-hydroxyoctadec-4-ene (36271-49-5)

Guidance literature:

With sodium acetate; In tetrahydrofuran; water; at 20 ℃; for 3h;

DOI:10.1016/S0040-4020(02)01092-X

Reference yield:

(2S,3R,4E)-2-(N-stearoylamino)-4-octadecene-1,3-diol (54336-64-0,95037-06-2,104826-38-2,123482-90-6,134731-78-5,136846-30-5,2304-81-6,252039-52-4) + 2,3,4,6-tetra-O-tetramethylsilyl-α-D-galactopyranosyl iodide (352432-47-4) → (2S,3R,4E)-1-(β-D-galactopyranosyloxy)-2-(octadecanoylamino)-3-hydroxyoctadec-4-ene (36271-49-5) + β-GalCer

Guidance literature:

(2S,3R,4E)-2-(N-stearoylamino)-4-octadecene-1,3-diol; 2,3,4,6-tetra-O-tetramethylsilyl-α-D-galactopyranosyl iodide; With N-ethyl-N,N-diisopropylamine; silver carbonate; In dichloromethane; toluene; at 110 ℃; for 12 - 48h; Molecular sieve;

With methanol; at 20 ℃; for 3h;

upstream raw materials:

psychosine

pentafluorophenol octadecanoate

Stearoyl chloride

stearic acid

Refernces

• 1、 Michieletti, Mario,Sillani, Laura,Panza, Luigi. "A properly protected sphingosine acceptor for helferich glycosylation". scheme or table. p. 2609 - 2612. Retrieved 2010/02/28.
• 2、 Conboy, John C.,McReynolds, Katherine D.,Gervay-Hague, Jacquelyn,Saavedra, S. Scott. "Quantitative measurements of recombinant HIV surface glycoprotein 120 binding to several glycosphingolipids expressed in planar supported lipid bilayers". . p. 968 - 977. Retrieved 2007/10/03.