745041-64-9

Upstream product

• 53081-30-4 tetra-O-benzyl-α-D-galactosyl bromide 
• 745041-56-9 (2S,3S,4R)-2-azido-3,4-O-isopropylidene-1,3,4-nonanetriol 
• 78153-79-4 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl fluoride 
• 745041-30-9 (2R,3S,4R)-1,3-O-benzylidene-2-O-methanesulfonyl-1,2,3,4-nonanetetrol 
• 745041-21-8 (2R,3S,4R)-1,3-O-benzylidene-1,2,3,4-nonanetetrol 
• 80924-06-7 1,3-O-benzylidene D-arabitol 
• 164576-08-3 1,3-O-benzylidene-5-O-toluenesulfonyl-D-arabitol 
• 164576-09-4 4,5-anhydro-1,3-O-benzylidene-D-arabinitol 
• 488-82-4 D-Arabitol 
• 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 

Downstream Products

• 745042-03-9 2-tricosanoylamino-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-D-ribo-1,3,4-nonanetriol 
• 745042-02-8 (2S,3S,4R)-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)-2-(tetracosanoylamino)nonane-3,4-diol 
• 745041-79-6 (2S,3S,4R)-3,4-O-isopropylidene-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2-tetracosanoylamino-1,3,4-nonanetriol 
• 383187-82-4 OCH 
• 956102-46-8 C₇₄H₁₁₃NO₉ 
• 956102-18-4 C₇₂H₁₀₉NO₉ 
• 956102-06-0 C₇₁H₁₀₇NO₉ 
• 745041-80-9 2-tricosanoylamino-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-3,4-O-isopropylidene-D-ribo-1,3,4-nonanetriol 
• 745042-04-0 2-docasanoylamino-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-D-ribo-1,3,4-nonanetriol 
• 745041-81-0 2-docasanoylamino-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-3,4-O-isopropylidene-D-ribo-1,3,4-nonanetriol 
• 956101-40-9 C₆₆H₉₇NO₉ 
• 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 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

GLYCOLIPID DERIVATIVES, PROCESS FOR PRODUCTION OF THE SAME, INTERMEDIATES FOR SYNTHESIS THEREOF, AND PROCESS FOR PRODUCTION OF THE INTERMEDIATES

Novel glycolipid derivatives, where the substituent of the sphingosine base part is a short carbon chain alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted aryl group or substituted or unsubstituted aralkyl group and

Total synthesis of an immunosuppressive glycolipid, (2S,3S,4R)-1-O- (α-D-galactosyl)-2-tetracosanoylamino-1,3,4-nonanetriol

(Chemical Equation Presented) A practical and efficient total synthesis of (2S,3S,4R)-1-O-(α-D-galactosyl)-2-tetracosanoylamino-1,3,4-nonanetriol, OCH 1b, a potential therapeutic candidate for Th1-mediated autoimmune diseases, is described. The synthesis