114299-45-5

Basic information

• Product Name: (2S,3R,4E)-2-Azido-3-(pivaloyloxy)-1-(triphenylmethyloxy)-4-octadecen
• Synonyms: (2S,3R,4E)-2-Azido-3-(pivaloyloxy)-1-(triphenylmethyloxy)-4-octadecen
• CAS NO: 114299-45-5
• Molecular Weight: 651.933
• Mol File: 114299-45-5.mol

Chemical Properties

• CAS DataBase Reference: (2S,3R,4E)-2-Azido-3-(pivaloyloxy)-1-(triphenylmethyloxy)-4-octadecen(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R,4E)-2-Azido-3-(pivaloyloxy)-1-(triphenylmethyloxy)-4-octadecen(114299-45-5)
• EPA Substance Registry System: (2S,3R,4E)-2-Azido-3-(pivaloyloxy)-1-(triphenylmethyloxy)-4-octadecen(114299-45-5)

Safety Data

• Hazardous Substances Data: 114299-45-5(Hazardous Substances Data)

Upstream product

• 103348-49-8 2-azido-sphingosine 
• 104826-27-9 <2(R),3(R),4E>-1,3-O-isopropylidene-4-octadecene-1,2,3-triol 
• 123-78-4 (2S,3R,4E)-2-amino-4-octadecene-1,3-diol 
• 104826-31-5 <2(S),3(R),4E>-2-azido-1,3-O-isopropylidene-4-octadecene-1,3-diol 
• 114275-39-7 (2R,3R,4E)-1,3-benzylidene-4-octadecene-1,2,3-triol 
• 114275-40-0 (2R,3R)-trans-2-azide-1,3-O-benzylidene-1,3-octadec-4-enediol 
• 25791-20-2 (n-tetradecyl)triphenylphosphonium bromide 
• 108283-57-4 (2S,3R,4E)-2-azido-1-(triphenylmethyl)-4-octadecene-1,3-diol 
• 3282-30-2 pivaloyl chloride 

Relevant articles and documents

Synthesis of Gb3 Glycosphingolipids with Labeled Head Groups: Distribution in Phase-Separated Giant Unilamellar Vesicles

The receptor lipid Gb3 is responsible for the specific internalization of Shiga toxin (STx) into cells. The head group of Gb3 defines the specificity of STx binding, and the backbone with different fatty acids is expected to influence its localization within membranes impacting membrane organization and protein internalization. To investigate this influence, a set of Gb3 glycosphingolipids labeled with a BODIPY fluorophore attached to the head group was synthesized. C24 fatty acids, saturated, unsaturated, α-hydroxylated derivatives, and a combination thereof, were attached to the sphingosine backbone. The synthetic Gb3 glycosphingolipids were reconstituted into coexisting liquid-ordered (lo)/liquid-disordered (ld) giant unilamellar vesicles (GUVs), and STx binding was verified by fluorescence microscopy. Gb3 with the C24:0 fatty acid partitioned mostly in the lo phase, while the unsaturated C24:1 fatty acid distributes more into the ld phase. The α-hydroxylation does not influence its partitioning.

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.