116467-63-1

Basic information

• Product Name: (4E,2S,3R)-1,3-Dihydroxy-2-((tert-b
• Synonyms: (4E,2S,3R)-1,3-Dihydroxy-2-((tert-b;[(1S,2R,3E)-2-Hydroxy-1-(hydroxyMethyl)-3-heptadecenyl]carbaMic Acid 1,1-DiMethylethyl Ester;[R-[R*,S*-(E)]]-[2-Hydroxy-1-(hydroxyMethyl)-3-heptadecenyl]carbaMic Acid 1,1-DiMethylethyl Ester
• CAS NO: 116467-63-1
• Molecular Formula: C₂₃H₄₅NO₄
• Molecular Weight: 399.6077
• Product Categories: Fatty Acid Derivatives & Lipids;Glycerols;Inhibitors;Protein Kinase Inhibitors and Activators;Glycerols, Fatty Acid Derivatives & Lipids
• Mol File: 116467-63-1.mol
• Article Data: 38

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (4E,2S,3R)-1,3-Dihydroxy-2-((tert-b(CAS DataBase Reference)
• NIST Chemistry Reference: (4E,2S,3R)-1,3-Dihydroxy-2-((tert-b(116467-63-1)
• EPA Substance Registry System: (4E,2S,3R)-1,3-Dihydroxy-2-((tert-b(116467-63-1)

Safety Data

• Hazardous Substances Data: 116467-63-1(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.

Upstream product

• 123-78-4 (2S,3R,4E)-2-amino-4-octadecene-1,3-diol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 263352-70-1 1-hydroxy-2-(S)-tert-butoxycarbonylamino-octadec-4-en-3-one 
• 221455-36-3 tert-butyl ((2S,3R,E)-1-((tert-butyldimethylsilyl)oxy)-3-hydroxy-octadec-4-en-2-yl)carbamate 
• 342655-72-5 tert-butyl (2S,3R,E)-2-(tert-butyldimethylsiloxy)-1-hydroxyoctadec-4-en-2-ylcarbamate 
• 498541-36-9 (2S,3S,4E)-2-N-tert-butoxycarbonylaminooctadec-1,3-O-di-(tert-butyl)silanediyl-4-ene-1,3-diol 
• 765-13-9 pentadec-1-yne 
• 102308-32-7 (4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 1026601-72-8 [2-(tert-butyl-diphenyl-silanyloxy)-1-triisopropylsilanyloxymethyl-heptadec-3-enyl]-carbamic acid tert-butyl ester 
• 115464-03-4 tert-butyl (4S)-4-[(1R,2E)-1-hydroxy-2-hexadecenyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 
• 117487-53-3 tert-butyl (1S,2R)-N-<2-hydroxy-1-(hydroxymethyl)-3-heptadecynyl>carbamate 
• 2766-43-0 N-tert-butyloxycarbonyl-L-serine methyl ester 
• 108149-63-9 4-hydroxymethyl-2,2-dimethyloxazolidine-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 

Downstream Products

• 342649-71-2 2,2-Dimethyl-propionic acid (E)-(2S,3R)-2-tert-butoxycarbonylamino-3-hydroxy-octadec-4-enyl ester 
• 4201-58-5 (2S,3R,4E)-2-(hexadecanoylamido)-4-octadecene-1,3-diol 
• 3102-57-6 N-acetyl-D-erythro-sphingosine 
• 140408-14-6 (2S,3R)-N-(tert-butoxycarbonyl)-<2-amino-1,3-dihydroxyoctadecane> 
• 2673-72-5 (2S,3R,E)-2-aminooctadec-4-ene-1,3-diol hydrochloride 
• 1196665-01-6 (2S,3R,4E)-2-amino-3-hydroxyoctadec-4-enyl-(4'-bromo-5'-hydroxy-2'-nitrophenyl)(phenyl)methyl hydrogen phosphate 
• 1196665-02-7 (4'-bromo-5'-hydroxy-2'-nitrophenyl)(phenyl)methyl-(2S,3R,4E)-3-hydroxy-2-palmitamidooctadec-4-enyl hydrogen phosphate 
• 1196664-99-9 (4S,5R,1''E)-tert-butyl-4-((((4'-bromo-5'-methoxy-2'-nitrophenyI)(phenyl)methoxy)(methoxy)phosphoryloxy)methyI)-2,2-dimethyl-5-(pentadec-1''-enyl)oxazolidine-3-carboxylate 
• 1196665-00-5 tert-butyl (4S,5R,1E)-4-((((4'-bromo-5'-methoxy-2'-nitrophenyl)(phenyl)methoxy)(methoxy)phosphoryloxy)methyl)-2,2-dimethyl-5-(pentadec-1-enyl)oxazolidine-3-carboxylate 
• 1196664-91-1 tert-butyl (4S,5R,1''E)-4-((((4'-bromo-5'-hydroxy-2'-nitrophenyl)(phenyl)methoxy)(hydroxy)phosphoryloxy)methyl)-2,2-dimethyl-5-(pentadec-1''-enyl)oxazolidine-3-carboxylate 
• 207516-23-2 tert-butyl (4S,5R,1'E)-4-(hydroxymethyl)-2,2-dimethyl-5-(pentadec-1'-enyl)-oxazolidine-3-carboxylate 
• 172213-38-6 (2S,3R,E)-1-(tert-butyldiphenylsilyloxy)-2-(N-tertbutyloxycarbonyl)aminooctadec-4-en-3-ol 
• 207516-26-5 (4S,5R)-4-{Bis-[1-(2-nitro-phenyl)-ethoxy]-phosphoryloxymethyl}-2,2-dimethyl-5-((E)-pentadec-1-enyl)-oxazolidine-3-carboxylic acid tert-butyl ester 
• 207516-11-8 Phosphoric acid (E)-(2S,3R)-2-amino-3-hydroxy-octadec-4-enyl ester bis-[1-(2-nitro-phenyl)-ethyl] ester 

Relevant articles and documents

A diversity oriented synthesis of D-erythro-sphingosine and siblings

An efficient building block-based synthetic protocol has been developed for the synthesis of 3-ketosphingoids with various chain lengths using cross metathesis of a Garner's aldehyde-derived α,β-unsaturated ketone as the key step. Stereoselective reduction of the biomimetic precursors thus obtained provided D-erythro-sphingosine and truncated anaogues in good overall yields.

Efficient synthesis of sphingosine-1-phosphonate and homo-sphingosine-1-phosphonate

Sphingosine can be selectively transformed into 2-N,3-O-protected 1-O-mesyl derivative 8. Transformation into the bromide, Michaelis-Arbusov reaction with trimethyl phosphite, and then removal of all protective groups with LiOH afforded sphingosine-1-phosphonate (4) in high overall yield. Chain extension of 8 with KCN and ensuing reduction led to homosphingosine derivative 10 and also to homo-1-deoxysphingosine (5). 1-O-Mesylation of 10 led via the same sequence of reactions finally to homo-sphingosine-1-phosphonate (6).

Preparation of Nitrogen Analogues of Ceramide and Studies of Their Aggregation in Sphingomyelin Bilayers

Ceramides can regulate biological processes probably through the formation of laterally segregated and highly packed ceramide-rich domains in lipid bilayers. In the course of preparation of its analogues, we found that a hydrogen-bond-competent functional group in the C1 position is necessary to form ceramide-rich domains in lipid bilayers [ Matsufuji; et al. Langmuir 2018 ]. Hence, in the present study, we newly synthesized three ceramide analogues: CerN3, CerNH2, and CerNHAc, in which the 1-OH group of ceramide is substituted with a nitrogen functionality. CerNH2 and CerNHAc are capable of forming hydrogen bonds in their headgroups, whereas CerN3 is not. Fluorescent microscopy observation and differential scanning calorimetry analysis disclosed that these ceramide analogues formed ceramide-rich phases in sphingomyelin bilayers, although their thermal stability was slightly inferior to that of normal ceramides. Moreover, wide-angle X-ray diffraction analysis showed that the chain packing structure of ceramide-rich phases of CerNHAc and CerN3 was similar to that of normal ceramide, while the CerNH2-rich phase showed a slightly looser chain packing due to the formation of CerNH3+. Although the domain formation of CerN3 was unexpected because of the lack of hydrogen-bond capability in the headgroup, it may become a promising tool for investigating the mechanistic link between the ceramide-rich phase and the ceramide-related biological functions owing to its Raman activity and applicability to click chemistry.

N-AS-triggered SPMs are direct regulators of microglia in a model of Alzheimer’s disease

Sphingosine kinase1 (SphK1) is an acetyl-CoA dependent acetyltransferase which acts on cyclooxygenase2 (COX2) in neurons in a model of Alzheimer’s disease (AD). However, the mechanism underlying this activity was unexplored. Here we show that N-acetyl sphingosine (N-AS) is first generated by acetyl-CoA and sphingosine through SphK1. N-AS then acetylates serine 565 (S565) of COX2, and the N-AS-acetylated COX2 induces the production of specialized pro-resolving mediators (SPMs). In a mouse model of AD, microglia show a reduction in N-AS generation, leading to decreased acetyl-S565 COX2 and SPM production. Treatment with N-AS increases acetylated COX2 and N-AS-triggered SPMs in microglia of AD mice, leading to resolution of neuroinflammation, an increase in microglial phagocytosis, and improved memory. Taken together, these results identify a role of N-AS in the dysfunction of microglia in AD.