1269616-94-5

Basic information

• Product Name: (2S,3S,4R)-2-azido-3,4-di-(benzoyloxy)-1-(α-D-galactopyranosyloxy)pentadecane
• Synonyms: (2S,3S,4R)-2-azido-3,4-di-(benzoyloxy)-1-(α-D-galactopyranosyloxy)pentadecane
• CAS NO: 1269616-94-5
• Molecular Weight: 671.788
• Mol File: 1269616-94-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2S,3S,4R)-2-azido-3,4-di-(benzoyloxy)-1-(α-D-galactopyranosyloxy)pentadecane(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S,4R)-2-azido-3,4-di-(benzoyloxy)-1-(α-D-galactopyranosyloxy)pentadecane(1269616-94-5)
• EPA Substance Registry System: (2S,3S,4R)-2-azido-3,4-di-(benzoyloxy)-1-(α-D-galactopyranosyloxy)pentadecane(1269616-94-5)

Safety Data

• Hazardous Substances Data: 1269616-94-5(Hazardous Substances Data)

Upstream product

• 372988-39-1 (2S,3S,4R)-2-azido-pentadecane-1,3,4-triol 
• 1269617-00-6 C₃₁H₄₉N₃O₃Si 
• 1269617-03-9 C₄₅H₅₇N₃O₅Si 
• 1269616-91-2 (2S,3S,4R)-2-azido-3,4-di-(benzoyloxy)-pentadecan-1-ol 
• 352432-47-4 2,3,4,6-tetra-O-tetramethylsilyl-α-D-galactopyranosyl iodide 
• 372988-38-0 (2R,3R,4R)-2-methanesulfonyloxy-pentadecane-1,3,4-triol 
• 1769-00-2 1,2,3,4,6-penta-O-trimethylsilyl-α-D-galactose 

Relevant articles and documents

Synthesis of truncated analogues of the iNKT cell agonist, α-galactosyl ceramide (KRN7000), and their biological evaluation

Stimulation of iNKT cells by α-galactosyl ceramide (α-GalCer), also known as KRN7000, and its truncated analogue OCH induces both Th1- and Th2-cytokines, with OCH inducing a Th2-cytokine bias. Skewing of the iNKT cells' response towards either a Th1- or Th2-cytokine profile offers potential therapeutic benefits. The length of both the acyl and the sphingosine chains in α-galactosyl ceramides is known to influence the cytokine release profile. We have synthesized analogues of α-GalCer with truncated sphingosine chains for biological evaluation, with particular emphasis on the Th1/Th2 distribution. Starting from a common precursor, d-lyxose, the sphingosine derivatives were synthesised via a straightforward Wittig condensation.