150338-90-2

Usage

Uses

Used in Pharmaceutical Industry:
(2R,3S,4E)-2-(acetylamino)-4-octadecen-1,3-diol is used as a potential therapeutic agent for the treatment of pain and inflammation due to its role in regulating these processes. Its endogenous presence in the body suggests that it may have a natural mechanism for modulating pain and inflammation, making it a promising candidate for pharmaceutical development.
Used in Neurodegenerative Disease Research:
In the field of neurodegenerative disease research, (2R,3S,4E)-2-(acetylamino)-4-octadecen-1,3-diol is used as a potential therapeutic agent for conditions such as Parkinson's disease. Its involvement in physiological processes and its presence in the brain make it a candidate for further study and development as a treatment for neurodegenerative disorders.
Used in Cancer Research:
(2R,3S,4E)-2-(acetylamino)-4-octadecen-1,3-diol is used as a subject of research in cancer studies, where it is being investigated for its potential therapeutic effects. Its bioactive properties and presence in various tissues suggest that it may have an impact on cancer progression or treatment.
Used in Obesity Research:
In the field of obesity research, (2R,3S,4E)-2-(acetylamino)-4-octadecen-1,3-diol is used as a target for studying its role in appetite and energy metabolism modulation. Its potential to influence these processes makes it a candidate for developing treatments or interventions for obesity and related metabolic disorders.

Upstream product

• 2482-37-3 (+/-)-erythro-1,3-diacetoxy-2-acetylamino-octadec-4c-ene 
• 128387-02-0 (2R,3S,4E)-2-acetylamino-1,3-diacetoxyoctadec-4-ene 
• 143516-94-3 N-{(1R,2R)-2-Methoxymethoxy-1-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-3-oxo-propyl}-acetamide 
• 143516-99-8 N-{(1R,2R)-3-Hydroxy-2-methoxymethoxy-1-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-propyl}-acetamide 
• 143516-95-4 N-{(E)-(1R,2S)-2-Methoxymethoxy-1-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-heptadec-3-enyl}-acetamide 
• 201340-33-2 N-((E)-(1R,2S)-2-Hydroxy-1-hydroxymethyl-heptadec-3-enyl)-acetamide 
• 6036-75-5 (2R,3S,4E)-2-aminooctadec-4-ene-1,3-diol 
• 75-36-5 acetyl chloride 
• 114697-01-7 (+/-)-N-(4t-pentadec-1-ynyl-2r-phenyl-[1,3]dioxan-5t-yl)-acetamide 
• 114697-01-7 (+/-)-N-(4c-pentadec-1-ynyl-2r-phenyl-[1,3]dioxan-5c-yl)-acetamide 
• 94676-99-0 N-((1RS,2RS)-2-hydroxy-1-hydroxymethyl-heptadec-3-ynyl)-acetamide 
• 94676-99-0 N-((1RS,2SR)-2-hydroxy-1-hydroxymethyl-heptadec-3-ynyl)-acetamide 

Downstream Products

• 2482-37-3 (+/-)-erythro-1,3-diacetoxy-2-acetylamino-octadec-4c-ene 
• 2482-37-3 (+/-)-threo-1,3-diacetoxy-2-acetylamino-octadec-4c-ene 

Relevant academic research and scientific papers

Chiral combinatorial preparation and biological evaluation of unique ceramides for inhibition of sphingomyelin synthase

Enantiomers or diastereomers of chiral bioactive compounds often exhibit different biological and toxicological properties. Here, we report the efficient synthesis of four stereoisomers of sphingosine and derivatization of unique chiral ceramides through a combinatorial chemistry by solid-phase activated resin ester. In addition, to test the effectivity of stereochemistry of ceramide, we demonstrated a cell-based assay of sphingomyelin synthase inhibition in the presence ofchiral unique ceramides, which suggested that libraries of this sort will be a rich source of biologically active synthetic molecules.

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

Syntheses of two pairs of enantiomeric C18-sphingosines and a palmitoyl analogue of gaucher spleen glucocerebroside

Sixteen kinds of chiral C4-epoxides [(-)-10a-d,(+)-10a-d,(-)-11a-d,(+)-11a-d], which are synthons in our synthetic strategy for complex lipids, have been prepared from (2Z)-2-butene-1,4-diol (6) by employing a Sharpless asymmetric epoxidation. By using the chiral C4-epoxides [(+)-10a,(-)-10a,(-)-11a,(+)-11a] as starting compounds, two pairs of enantiomeric (D-erythro, L-erythro, D-threo, and L-threo)-C18-sphingosines (1, 2, 3, 4) have been synthesized via a regioselective ring-opening of the epoxide ring with azide anion followed by reduction of the azide group to an amino group and a Wittig reaction. Furthermore, D-erythro-C18-sphingosine (1) has been converted to a palmitoyl analogue (5a) of Gaucher spleen glucocerebroside (5) through a reaction pathway including successive condensations with palmitic acid and D-glucose.

A novel, efficient synthesis of (±)-erythro-sphingosine

A stereoselective synthesis of (±)-erythro-sphingosine triacetate (1) is described. The key reaction that determines the right stereochemistry is the iodocyclization of 1-trichloroacetimido-(2E,4E)-octadecadiene (5). The 4,5-dihydro-1,3-oxazine (6) through cleavage with HCl and treatment with Amberlyst A 26 in the AcO- form, followed by full acetylation, affords (1) in good yield.