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

Chemical Properties

White Crystalline Solid

Uses

The N-Boc protected Sphingosine, a selective inhibitor of protein kinase C activity and phorbol dibutyrate binding in vitro in human platelets; does not inhibit protein kinase A or myosin light chain kinase; inhibits calmodulin-dependent enzymes

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

• 24424-99-5 di-tert-butyl dicarbonate 
• 6036-75-5 (2R,3S,4E)-2-aminooctadec-4-ene-1,3-diol 
• 114301-34-7 tert-butyl (S)-4-((R)-1-hydroxyallyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 102308-32-7 (4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 95715-86-9 (S)-2,2-dimethyl-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 4-methyl ester 
• 2766-43-0 N-tert-butyloxycarbonyl-L-serine methyl ester 
• 3262-72-4 (S)-N-(tert-butoxycarbonyl)serine 
• 765-13-9 pentadec-1-yne 
• 765-09-3 1-bromotridecane 
• 609812-01-3 (4R,5S)-4-[(1R)-1-azido-2-(benzyloxy)ethyl]-2,2-dimethyl-5-[(E)-1-(4-methylphenylsulfonyl)-3-tetradecenyl]-1,3-dioxolane 
• 609811-98-5 2-azido-2-[(4R,5S)-2,2-dimethyl-5-[(E)-1-(4-methylphenylsulfanyl)-3-tetradecenyl]-1,3-dioxolan-4-yl]ethyl benzyl ether 
• 609811-97-4 Trifluoro-acetic acid [(4S,5R)-5-((R)-1-azido-2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-p-tolylsulfanyl-methyl ester 
• 609811-96-3 (4R,5S)-4-[(1R)-1-azido-2-(benzyloxy)ethyl]-2,2-dimethyl-5-(4-methylphenylsulfinylmethyl)-1,3-dioxolane 
• 609811-95-2 (2S,3R,4R)-4-azido-5-benzyloxy-1-(4-methylphenylsulfinyl)pentane-2,3-diol 

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.

Novel, short, stereospecific synthesis of lyxo-(2R,3R,4R)-phytosphingosine and erythro-(2R,3S)-sphingosine

lyxo-Phytosphingosine and erythro-sphingosine have been elaborated from a common intermediate. The key step in the reaction sequence involves stereo- and regiospecific functionalization of an olefin by intramolecular nucleophilic sulfinyl group participat