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

Description

(4E,2S,3R)-1,3-Dihydroxy-2-((tert-butyldimethylsilyl)oxy)-4-hexadecene-1-yne is a complex organic compound with a unique structure that features a hexadecene backbone with a triple bond, a dihydroxy group, and a tert-butyldimethylsilyl ether protecting group. (4E,2S,3R)-1,3-Dihydroxy-2-((tert-b is characterized by its stereochemistry, with the 4E, 2S, and 3R configurations indicating the spatial arrangement of its atoms. Its chemical properties include being a white crystalline solid.

Uses

Used in Pharmaceutical Industry:
(4E,2S,3R)-1,3-Dihydroxy-2-((tert-butyldimethylsilyl)oxy)-4-hexadecene-1-yne is used as a selective inhibitor of protein kinase C activity and phorbol dibutyrate binding in vitro in human platelets. Its application in this industry is due to its ability to modulate specific cellular signaling pathways, which can have therapeutic effects on various diseases.
Used in Chemical Synthesis:
(4E,2S,3R)-1,3-Dihydroxy-2-((tert-butyldimethylsilyl)oxy)-4-hexadecene-1-yne is used as a key intermediate in the synthesis of various complex organic compounds. Its unique structure and functional groups make it a valuable building block for the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Research and Development:
(4E,2S,3R)-1,3-Dihydroxy-2-((tert-butyldimethylsilyl)oxy)-4-hexadecene-1-yne is used as a research compound to study the structure-activity relationships of protein kinase C inhibitors and other biologically active molecules. Its unique stereochemistry and functional groups provide valuable insights into the design and optimization of new drug candidates.
Used in Drug Delivery Systems:
(4E,2S,3R)-1,3-Dihydroxy-2-((tert-butyldimethylsilyl)oxy)-4-hexadecene-1-yne can be used in the development of drug delivery systems to improve the bioavailability and therapeutic efficacy of various drugs. Its unique structure and functional groups can be exploited to design novel drug carriers and delivery platforms.

Upstream product

• 765-13-9 pentadec-1-yne 
• 102308-32-7 (4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 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 
• 129293-64-7 (S)-3-(tert-butoxycarbonyl)-4-(1-oxo-hexadec-2-enyl)-2,2-dimethyloxazolidine 
• 1401216-98-5 (S)-tert-butyl 4-acryloyl-2,2-dimethyloxazolidine-3-carboxylate 
• 256650-51-8 (4S)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-<1-hydroxy-2-propenyl>oxazolidine 
• 263558-18-5 tert-butyl 4-[(1R,2E)-1-benzoyloxyhexadec-2-enyl]-2,2-dimethyloxazolidine-3-carboxylate 
• 13360-61-7 1-pentadecene 
• 299172-59-1 N-(tert-butoxycarbonyl)-3-O-benzoyl-D-erythro-sphingosine 
• 114301-34-7 tert-butyl (S)-4-((R)-1-hydroxyallyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 244777-36-4 (2S,3S,5RS)-2-tert-butoxycarbonylamino-3-tert-butyldiphenylsilyloxy-5-p-tolylsulfonyl-1-triisopropylsilyloxyoctadecan-4-one 
• 395069-17-7 (2S,3S,4Z)-2-tert-butoxycarbonylamino-3-tert-butyldiphenylsilyloxy-4-trifluoromethanesulfonyloxy-1-triisopropylsilyloxyoctadec-4-ene 

Downstream Products

• 2673-72-5 (2S,3R,E)-2-aminooctadec-4-ene-1,3-diol hydrochloride 
• 140408-14-6 (2S,3R)-N-(tert-butoxycarbonyl)-<2-amino-1,3-dihydroxyoctadecane> 
• 3102-57-6 N-acetyl-D-erythro-sphingosine 
• 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 
• 4201-58-5 (2S,3R,4E)-2-(hexadecanoylamido)-4-octadecene-1,3-diol 
• 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 
• 26993-30-6 Sphingosine-1-phosphate 

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.

Liposomal FRET Assay Identifies Potent Drug-Like Inhibitors of the Ceramide Transport Protein (CERT)

Ceramide transfer protein (CERT) mediates non-vesicular transfer of ceramide from endoplasmic reticulum to Golgi apparatus and thus catalyzes the rate-limiting step of sphingomyelin biosynthesis. Usually, CERT ligands are evaluated in tedious binding assays or non-homogenous transfer assays using radiolabeled ceramides. Herein, a facile and sensitive assay for CERT, based on F?rster resonance energy transfer (FRET), is presented. To this end, we mixed donor and acceptor vesicles, each containing a different fluorescent ceramide species. By CERT-mediated transfer of fluorescent ceramide, a FRET system was established, which allows readout in 96-well plate format, despite the high hydrophobicity of the components. Screening of a 2 000 compound library resulted in two new potent CERT inhibitors. One is approved for use in humans and one is approved for use in animals. Evaluation of cellular activity by quantitative mass spectrometry and confocal microscopy showed inhibition of ceramide trafficking and sphingomyelin biosynthesis.