609812-03-5

Basic information

• Product Name: N-BOC-ERYTHRO-SPHINGOSINE
• Synonyms: (2S,3R,4E)-2-TERT-BUTYLOXYCARBONYLAMINO-4-OCTADECEN-1,3-DIOL;N-BOC-ERYTHRO-SPHINGOSINE
• CAS NO: 609812-03-5
• Molecular Formula: C₂₃H₄₅NO₄
• Molecular Weight: 399.61
• Product Categories: Mixed Fatty Acids;Fatty Acid Derivatives & Lipids;Glycerols;Inhibitors;Protein Kinase Inhibitors and Activators
• Mol File: 609812-03-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 59-60°C
• Boiling Point: 536.6°C at 760 mmHg
• Flash Point: 278.3°C
• Appearance: /
• Density: 0.974g/cm³
• Vapor Pressure: 9.42E-14mmHg at 25°C
• Refractive Index: 1.482
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Sparingly), Dichloromethane (Slightly), Ethyl Acetate (Slightly), Me
• Stability: Freezer
• CAS DataBase Reference: N-BOC-ERYTHRO-SPHINGOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-BOC-ERYTHRO-SPHINGOSINE(609812-03-5)
• EPA Substance Registry System: N-BOC-ERYTHRO-SPHINGOSINE(609812-03-5)

Safety Data

• Hazardous Substances Data: 609812-03-5(Hazardous Substances Data)

Usage

Description

N-BOC-ERYTHRO-SPHINGOSINE, also known as N-BOC protected Sphingosine, is a white crystalline solid with significant biological and chemical properties. It is a selective inhibitor of protein kinase C activity and phorbol dibutyrate binding in vitro in human platelets. N-BOC-ERYTHRO-SPHINGOSINE does not inhibit protein kinase A or myosin light chain kinase, and it also inhibits calmodulin-dependent enzymes.

Uses

Used in Pharmaceutical Industry:
N-BOC-ERYTHRO-SPHINGOSINE is used as a selective inhibitor for protein kinase C activity and phorbol dibutyrate binding in vitro in human platelets. Its application is crucial for studying the role of these proteins in various cellular processes and their potential as therapeutic targets.
Used in Research and Development:
In the field of research and development, N-BOC-ERYTHRO-SPHINGOSINE is used as a valuable tool for understanding the mechanisms of protein kinase C, calmodulin-dependent enzymes, and other related proteins. Its selective inhibition properties make it an essential compound in the development of new drugs and therapies targeting these proteins.
Used in Drug Design and Synthesis:
N-BOC-ERYTHRO-SPHINGOSINE is used as a starting material or intermediate in the synthesis of various drugs and pharmaceutical compounds. Its unique chemical properties and selective inhibition capabilities make it a valuable component in the development of novel therapeutic agents.
Used in Diagnostic Applications:
In the diagnostic industry, N-BOC-ERYTHRO-SPHINGOSINE can be employed as a reagent or reference compound for the detection and quantification of protein kinase C and related enzymes. Its specificity and selectivity make it a useful tool in the development of diagnostic tests and assays.
Used in Biochemical and Cellular Studies:
N-BOC-ERYTHRO-SPHINGOSINE is used as a research compound in biochemical and cellular studies to investigate the roles of protein kinase C, calmodulin-dependent enzymes, and other related proteins in various biological processes. Its ability to selectively inhibit these proteins aids in understanding their functions and potential implications in disease development.

InChI:InChI=1/C23H45NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-21(26)20(19-25)24-22(27)28-23(2,3)4/h17-18,20-21,25-26H,5-16,19H2,1-4H3,(H,24,27)/b18-17+/t20-,21+/m1/s1

Upstream product

• 928302-10-7 tert-butyl (1R,2S)-N-[2-hydroxy-1-(hydroxymethyl)-3-heptadecynyl]-carbamate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 6036-75-5 (2R,3S,4E)-2-aminooctadec-4-ene-1,3-diol 
• 609812-02-4 2-(tert-butoxycarbonylamino)-2-{(4R,5S)-2,2-dimethyl-5-[(E)-1-(4-methylphenylsulfonyl)tetradecyl]-1,3-dioxolan-4-yl}-1-ethanol 
• 898232-47-8 tert-butyl (2R,3S,E)-2-(tert-butyldimethylsiloxy)-1-hydroxyoctadec-4-en-2-ylcarbamate 
• 3262-72-4 (R)-N-tert-butoxycarbonyl serine 
• 95715-85-8 2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester 
• 95715-87-0 (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine 
• 108149-60-6 methyl [(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]carboxylate 
• 524939-19-3 tert-butyl (4R,1'S)-2,2-dimethyl-4-(1'-hydroxyhexadec-2'-ynyl)oxazolidione-3-carboxylate 
• 898232-34-3 (2R,3R)-methyl 3-(tert-butoxycarbonylamino)-2-(tert-butyldimethylsiloxy)-3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]propanoate 
• 898232-42-3 tert-butyl (2S,3R,4S,E)-2-(tert-butyldimethylsiloxy)-1,2-dihydroxynonadec-4-en-2-ylcarbamate 
• 898232-38-7 (4S)-4-[(1R,2S,E)-1-(tert-butoxycarbonylamino)-2-(tert-butyldimethylsiloxy)-3-heptadecenyl]-2,2-dimethyl-1,3-dioxolane 
• 110426-21-6 (E)-5-Benzyloxy-1-((R)-toluene-4-sulfinyl)-pent-3-en-2-one 

Downstream Products

• 172213-38-6 (2S,3R,E)-1-(tert-butyldiphenylsilyloxy)-2-(N-tertbutyloxycarbonyl)aminooctadec-4-en-3-ol 

Relevant articles and documents

Enantioselective Synthesis of Aminodiols by Sequential Rhodium-Catalysed Oxyamination/Kinetic Resolution: Expanding the Substrate Scope of Amidine-Based Catalysis

Regio- and stereoselective oxyamination of dienes through a tandem rhodium-catalysed aziridination–nucleophilic opening affords racemic oxazolidinone derivatives, which undergo a kinetic resolution acylation process with amidine-based catalysts (ABCs) to achieve s values of up to 117. This protocol was applied to the enantioselective synthesis of sphingosine.

Enantiodivergent synthesis of D- and L-erythro-sphingosines through Mannich-type reactions of N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone

The addition of a 2-silyloxy silylketene acetal to N-benzyl-2,3-O- isopropylidene-D-glyceraldehyde nitrone (Mannich-type reaction) can be stereocontrolled to give 2S,3S,4S and 2R,3R,4S adducts as major compounds, depending on whether the reaction is activated with zinc(II) triflate or tin-(IV) chloride, respectively. The corresponding major adducts were used for preparing diastereomeric polyhydroxy-β-aminoesters that were further converted into suitable orthogonally protected enantiomeric D- and L-erythro-sphingosines.

Syntheses of sphingosine-1-phosphate stereoisomers and analogues and their interaction with EDG receptors.

Sphingosine-1-phosphate (S1P) is considered to be an important regulator of diverse biological processes acting as a natural ligand to EDG receptors. As a preliminary study to develop potent and selective agonist and antagonist for EDG receptors, we report synthesis of S1P stereoisomers and analogues and their binding affinities to EDG-1, -3, and -5.