114275-41-1

Basic information

• Product Name: 2-AZIDO-1-PIVALOYL-D-ERYTHRO-SPHINGOSINE
• Synonyms: 2-AZIDO-1-PIVALOYL-D-ERYTHRO-SPHINGOSINE;(2S,3R,4E)-2-AZIDO-1-PIVALOYLOXY-4-OCTADECENE-3-OL;[R-[R*,S*-(E)]]-2,2-DiMethyl-propanoic Acid 2-Azido-3-hydroxy-4-octadecenyl Ester
• CAS NO: 114275-41-1
• Molecular Formula: C23H43N3O3
• Molecular Weight: 409.61
• Product Categories: Mixed Fatty Acids;Fatty Acid Derivatives & Lipids;Glycerols;Inhibitors;Protein Kinase Inhibitors and Activators
• Mol File: 114275-41-1.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Solubility: Acetone, Dichloromethane, Methanol
• CAS DataBase Reference: 2-AZIDO-1-PIVALOYL-D-ERYTHRO-SPHINGOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AZIDO-1-PIVALOYL-D-ERYTHRO-SPHINGOSINE(114275-41-1)
• EPA Substance Registry System: 2-AZIDO-1-PIVALOYL-D-ERYTHRO-SPHINGOSINE(114275-41-1)

Safety Data

• Hazardous Substances Data: 114275-41-1(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Oil

Uses

A derivative of 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 kina se; inhibits calmodulin-dependent enzymes; natural isomer of sphingosine.

Upstream product

• 103348-49-8 2-azido-sphingosine 
• 3282-30-2 pivaloyl chloride 
• 25791-20-2 (n-tetradecyl)triphenylphosphonium bromide 
• 114275-40-0 (2R,3R)-trans-2-azide-1,3-O-benzylidene-1,3-octadec-4-enediol 
• 114275-39-7 (2R,3R,4E)-1,3-benzylidene-4-octadecene-1,2,3-triol 
• 104826-27-9 <2(R),3(R),4E>-1,3-O-isopropylidene-4-octadecene-1,2,3-triol 
• 104826-31-5 <2(S),3(R),4E>-2-azido-1,3-O-isopropylidene-4-octadecene-1,3-diol 

Downstream Products

• 114275-42-2 (2S,3R,4E)-2-Azido-3-(tert-butyldimethylsilyloxy)-1-(pivaloyloxy)-4-octadecen 
• 114299-64-8 (2S,3S,4E)-2-azido-3-O-(tert-butyldimethylsilyl)-4-octadecen-1,3-diol 

Relevant articles and documents

Synthesis of Sphingosines, 4. - Synthesis of erythro-Sphingosines via Their Azido Derivatives

The 2,4-O-protected D-threoses 3a and 3b were obtained from D-galactose and D-xylose, respectively, in two-step procedures.Wittig reaction in the presence of an excess of lithium bromide afforded the trans-enetriols 4aA, 4aB, and 4bA.Triflate activation of the unprotected 2-hydroxy group, azide group introduction, and cleavage of the O-protective groups yielded the azidosphingosines 6A,B which provide after azide group reduction the D-erythro-sphingosines 7A,B.For the glycosphingolipid synthesis through azidosphingosine glycosylation, compound 6A was transformed by 1-O tritylation, 3-O protection, and subsequent 1-O detritylation into the 3-O-protected azidosphingosines 11α-11γ.