956102-18-4

Upstream product

• 745041-64-9 (2S,3S,4R)-2-azido-3,4-O-isopropylidene-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1,3,4-nonanetriol 
• 745041-56-9 (2S,3S,4R)-2-azido-3,4-O-isopropylidene-1,3,4-nonanetriol 
• 570414-15-2 (2R,3R,4R)-2-O-methanesulfonyl-1,2,3,4-nonanetetrol 
• 570414-16-3 (2S,3S,4R)-2-azido-nonane-1,3,4-triol 
• 942623-41-8 C₁₇H₂₆O₆S 
• 956028-66-3 C₁₆H₂₄O₄ 
• 918867-23-9 4,5-anhydro-1,3-O-benzylidene-D-arabitol 
• 506-46-7 1-hexacosanoic acid 
• 745041-72-9 (2S,3S,4R)-2-amino-3,4-O-isopropylidene-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1,3,4-nonanetriol 

Relevant academic research and scientific papers

Synthesis and biological evaluation of truncated α-galactosylceramide derivatives focusing on cytokine induction profile

A series of truncated analogs of α-galactosylceramide with altered ceramide moiety was prepared, and evaluated for Th2-biased response in the context of IL-4/IFN-γ ratio. Phytosphingosine-modified analogs including cyclic, aromatic and ethereal compounds

Synthesis of α-galactosyl ceramide (KRN7000) and analogues thereof via a common precursor and their preliminary biological assessment

(Chemical Equation Presented) A new practical synthesis of α-GalCer and of its analogues is presented, opening the chance to easily modify the sphingosine chain. The common precursor is a disaccharide, obtained by coupling tetra-O-benzyl-D-galactose with allyl 2,3-O-isopropylidene-D-lyxofuranoside. Introduction of alkyl chains via Wittig reaction (for α-GalCer and OCH) or via Williamson reaction (for oxa analogues) followed by standard synthetic steps allows one to efficiently obtain such compounds. The analogues are able to activate iNKT cells when presented by CD1d expressing cells.

Minimum structure requirement of immunomodulatory glycolipids for predominant Th2 cytokine induction and the discovery of non-linear phytosphingosine analogs

Analogs of immunomodulatory glycolipid OCH (2) were prepared and minimum structure requirement to exhibit equivalent profiles was disclosed. Analogs bearing non-linear hydrocarbon chain in the phytosphingosine moiety (18, 19) were shown for the first time