36271-49-5

Usage

Uses

Used in Pharmaceutical Industry:
N-stearoyl cerebroside is used as a pharmaceutical agent for its immunostimulatory and anti-tumor properties. It is particularly effective in promoting the regulation of nerve cells, modulating protein kinase C activities, and regulating hormone receptor functions.
Used in Cancer Treatment:
N-stearoyl cerebroside is used as a cancer treatment agent for its significant anti-tumor activity in mice with liver metastasis of the Colon26 adenocarcinoma. It has the potential to be further developed and utilized in cancer therapies targeting various types of cancer.

InChI:InChI=1/C42H81NO8/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-38(46)43-35(34-50-42-41(49)40(48)39(47)37(33-44)51-42)36(45)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h29,31,35-37,39-42,44-45,47-49H,3-28,30,32-34H2,1-2H3,(H,43,46)/b31-29+/t35-,36+,37?,39-,40-,41-,42+/m0/s1

Upstream product

• 2238-90-6 psychosine 
• 112-76-5 Stearoyl chloride 
• 54336-64-0 (2S,3R,4E)-2-(N-stearoylamino)-4-octadecene-1,3-diol 
• 352432-47-4 2,3,4,6-tetra-O-tetramethylsilyl-α-D-galactopyranosyl iodide 
• 1535186-28-7 (2S,3S,4S)-2-(tetrachlorophthalimido)-1,3-(4-methoxybenzylidene)-4-iodooctadecane 
• 1535186-29-8 (2S,3R,4E)-2-(tetrachlorophthalimido)-1,3-(4-methoxybenzylidene)octadec-4-ene 
• 1535186-30-1 (2S,3R,4E)-2-(tetrachlorophthalimido)-4-octadecen-1,3-diol 
• 1535186-32-3 (2S,3R,4E)-2-(tetrachlorophthalimido)-1-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-4-octadecen-1,3-diol 
• 554-62-1 D-ribo-phytosphingosine 
• 1535186-19-6 (2S,3S,4R)-2-(tetrachlorophthalimido)-octadecan-1,3,4-triol 
• 1200446-80-5 C₇₀H₉₇NO₁₂ 
• 1535186-34-5 C₅₂H₆₃NO₁₁ 
• 57-11-4 stearic acid 
• 1535186-27-6 C₃₄H₄₃Cl₄NO₆ 

Relevant academic research and scientific papers

Protected sphingosine from phytosphingosine as an efficient acceptor in glycosylation reaction

A convenient, simple, and high-yielding five-step synthesis of a sphingosine acceptor from phytosphingosine is reported, and its behavior in glycosylation reactions is described. Different synthetic paths to sphingosine acceptors using tetrachlorophthalimide as a protecting group for the sphingosine amino function and different glycosylation methods have been explored. Among the acceptors tested, the easiest accessible acceptor, unprotected on the two hydroxyl groups in positions 1 and 3, was regioselectively glycosylated on the primary position, the regioselectivity depending on the donor used.

A properly protected sphingosine acceptor for helferich glycosylation

The synthesis and some examples of glycosylations of a properly protected sphingosine is presented. This compound is suitable for the preparation of glycosphingolipids. It has been used for the synthesis of -mannosylceramide and sulfatide exploiting the anchimeric assistance to address the stereochemistry of the glycosidic bond.

ONE-POT SYNTHESIS OF ALPHA/BETA-O-GLYCOLIPIDS

The present invention provides a one-pot method of preparing an unprotected α-O-glycolipid. The first step involves contacting a protected α-iodo sugar with a catalyst and a lipid comprising a hydroxy group, under conditions sufficient to prepare a protected α- O-glycolipid. The second step involves deprotecting the protected α-O-glycolipid under conditions sufficient to prepare the unprotected α-O-glycolipid, wherein the contacting and deprotecting steps are performed in a single vessel. The present invention also provides a one-pot method of preparing an unprotected β-O-glycolipid following the steps for the preparation of the unprotected α-O-glycolipid.

Quantitative measurements of recombinant HIV surface glycoprotein 120 binding to several glycosphingolipids expressed in planar supported lipid bilayers

The interaction of recombinant HIV-1 surface glycoprotein gp120 (rgp120) with natural isolates of lactosylceramide (LacCer), glucosylceramide (GcCer), and galactosylceramide (GaCer) has been quantitatively measured under equilibrium conditions using total

CD1a-binding glycosphingolipids stimulating human autoreactive T-cells: Synthesis of a family of sulfatides differing in the acyl chain moiety

Native sulfatide (a mixture of 3-sulfated β-D-galactopyranosylceramides with different fatty acids at the ceramide moiety) is an antigen presented by CD1a proteins. Herein the preparation of four sulfatides, which are constituents of the natural mixture a

The synthesis and biological characterization of a ceramide library

A facile synthesis of a combinatorial ceramide library and their activities in the NF-κB pathway and in apoptosis induction/prevention were demonstrated. A novel NF-κB activating molecule was discovered among ceramide containing β-galactose, and the structural requirements of ceramides for apoptosis induction was elucidated. Copyright