108283-57-4

Basic information

• Product Name: (2S,3R,4E)-2-azido-1-(triphenylmethyl)-4-octadecene-1,3-diol
• Synonyms: (2S,3R,4E)-2-azido-1-(triphenylmethyl)-4-octadecene-1,3-diol
• CAS NO: 108283-57-4
• Molecular Weight: 567.815
• Mol File: 108283-57-4.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: (2S,3R,4E)-2-azido-1-(triphenylmethyl)-4-octadecene-1,3-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R,4E)-2-azido-1-(triphenylmethyl)-4-octadecene-1,3-diol(108283-57-4)
• EPA Substance Registry System: (2S,3R,4E)-2-azido-1-(triphenylmethyl)-4-octadecene-1,3-diol(108283-57-4)

Safety Data

• Hazardous Substances Data: 108283-57-4(Hazardous Substances Data)

Upstream product

• 123-78-4 (2S,3R,4E)-2-amino-4-octadecene-1,3-diol 
• 103348-49-8 2-azido-sphingosine 
• 76-83-5 trityl chloride 
• 104826-31-5 <2(S),3(R),4E>-2-azido-1,3-O-isopropylidene-4-octadecene-1,3-diol 
• 104826-27-9 <2(R),3(R),4E>-1,3-O-isopropylidene-4-octadecene-1,2,3-triol 
• 114275-39-7 (2R,3R,4E)-1,3-benzylidene-4-octadecene-1,2,3-triol 
• 124313-98-0 (2R,3R,4E)-1,3-benzylidene-2-methanesulfonyl-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 
• 112-71-0 1-Bromotetradecane 

Downstream Products

• 103348-50-1 (2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol 
• 52050-17-6 Glucosylsphingosine 
• 74365-77-8 glucosylceramide 
• 108283-59-6 (2S,3R,4E)-2',3',4',6'-tetraacetyl-β-D-glucopyranosyl-(1'<->1)-2-azido-3-benzoyl-4-octadecene-1,3-diol 
• 127861-88-5 (2S,3R,4E)-2-azido-3-O-(tert-butyldiphenylsilyl)-4-octadecene-1,3-diol 
• 141317-38-6 (2S,3R,4E)-2-(hexadecanoylamino)-3-(isobutanoyloxy)-1-<2,3,6-tri-O-acetyl-4,7-anhydro-4-C-(hydroxymethyl)-β-D-galactopyranosyloxy>-4-octadecene 
• 141250-04-6 (2S,3R,4E)-2-(hexadecanoylamino)-3-(isobutanoyloxy)-1-<2,3,6-tri-O-acetyl-4,7-anhydro-4-C-(hydroxymethyl)-β-D-glucopyranosyloxy>-4-octadecene 
• 4201-63-2 (2S,3R,4E)-[4'-O-(β-D-galactopyranosyl)-β-D-glucopyranosyl]-(1'->1)-2-(hexadecanoylamido)-4-octadecene-1,3-diol 
• 172340-52-2 Benzoic acid (E)-(R)-1-[(S)-1-azido-2-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-ethyl]-hexadec-2-enyl ester 
• 152386-92-0 (2S,3R,4E)-2-azido-3-(4-methoxybenzyl)-4-octadecen-1,3-diol 
• 853055-37-5 (2S,3R,4E)-3-O-para-methoxybenzyl-1-O-(2,3,4,6-tetra-0-benzyl)-α-D-galactopyranosyl-2-(N-octadecanosylamino)-4-octadecene 
• 853055-33-1 (2S,3R,4E)-2-azido-3-O-para-methoxybenzyl-1-O-(2,3,4,6-tetra-O-benzyl-D-galactopyranosyl)-4-octadecene 
• 853055-35-3 (2S,3R,4E)-2-amino-3-O-para-methoxybenzyl-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-4-octadecene 
• 853055-39-7 (2S,3R,4E)-2-azido-3-O-para-methoxybenzyl-1-O-D-galactopyranosyl-4-octadecene 

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.

A modular synthesis of alkynyl-phosphocholine headgroups for labeling sphingomyelin and phosphatidylcholine

(Figure Presented) A general route to phospho- and sphingolipids that incorporate an alkyne in the phosphocholine headgroup is described. The strategy preserves the ammonium functionality of the phosphocholine and can be easily modified to introduce desir

Efficient synthesis of α-galactosyl ceramide analogues using glycosyl iodide donors

(Chemical Equation Presented) The combination of reactive galactosyl iodide donors with electron-rich acceptor lipids provides highly stereoselective and efficient routes to α GalCer analogues. Using per-O-silylated donors, key intermediates can be obtain