95335-94-7

Upstream product

• 172847-85-7 (2R,3R,4S,5R,6S)-2-((benzoyloxy)methyl)-6-(p-tolylthio)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate 
• 34382-11-1 (2R)-1-O-(2′,3′,4′,6′-tetra-O-acetyl-β-D-glucopyranosyl)glycerol 
• 76739-15-6 1,2-O-isopropylidene-3-O-(β-D-glucopyranosyl)-sn-glycerol 
• 34382-09-7 <(4S)-2,2-dimethyl-1,3-dioxolan-4-yl>methyl tetra-O-acetyl-β-D-glucopyranoside 
• 58438-08-7 (2R)-1,2-di-O-benzyl-3-O-(2′,3′,4′,6′-tetra-O-acetyl-β-D-glucopyranosyl)glycerol 
• 74808-10-9 O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate 
• 59531-24-7 2,3,4,6-tetra-O-benzyl-D-glucopyranoside 
• 95335-92-5 (2R)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2,3-O-isopropylideneglycerol 
• 67773-43-7 2,3,4,6-tetra-O-benzyl-α/β-D-glucopyranosyl bromide 
• 76679-67-9 (2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-{2,3-bis-[((E)-but-2-enyl)oxy]-propoxy}-tetrahydro-pyran 

Downstream Products

• 55941-98-5 Hexadecanoic acid 1-hexadecanoyloxymethyl-2-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-ethyl ester 
• 156832-45-0 (2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2-O-palmitoyl-3-O-<(2-bromoethoxy)benzoxyphosphoryl>glycerol 
• 156832-46-1 (2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2-O-palmitoyl-3-O-phosphatidylcholinylglycerol 
• 1053700-96-1 Hexadecanoic acid (S)-1-[(2-bromo-ethoxy)-chloro-phosphoryloxymethyl]-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-ethyl ester 
• 156832-41-6 (2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2-O-palmitoyl-3-O-(tert-butyldimethylsilyl)glycerol 
• 156832-42-7 (2R)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2-O-palmitoylglycerol 
• 156832-43-8 (2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-3-O-palmitoylglycerol 
• 156832-40-5 (2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-3-O-(tert-butyldimethylsilyl)glycerol 

Relevant academic research and scientific papers

Mycobacterium tuberculosis β-gentiobiosyl diacylglycerides signal through the pattern recognition receptor Mincle: Total synthesis and structure activity relationships

Mycobacterium tuberculosis H37Ra produces a range of immunogenic β-gentiobiosyl diacylglycerides. We report the total synthesis of several candidate structures and show that these compounds signal weakly through mouse, but not human, Mincle. Structure-activity relationships reveal a striking dependence upon acyl chain length for gentiobiosyl diacylglyceride signalling through Mincle. Significantly, a truncated β-glucosyl diglyceride was shown to provide potent signalling through both human and mouse Mincle and could activate murine bone marrow derived dendritic cells.

A hydrophobic disordered peptide spontaneously anchors a covalently bound RNA hairpin to giant lipidic vesicles

The attraction of nucleic acids to lipidic compartments is the first step for carriers of potentially inheritable information to self-organise in functionalised synthetic cells. Confocal fluorescence imaging shows that a synthetic amphiphilic peptidyl RNA molecule spontaneously accumulates at the outer bilayer membranes of phospho- and glycolipidic giant vesicles. Cooperatively attractive interactions of -3.4 to -4.0 kcal mol-1 between a random coil hydrophobic peptide and lipid membranes can thus pilot lipophobic RNA to its compartmentation. The separation of mixed lipid phases in the membranes further enhances the local concentration of anchored RNA. the Partner Organisations 2014.

Synthesis of (2R)- and (2S)-β-D-glucopyranos-1-yl-2-O-palmitoyl-3-O-phosphatidylcholinylglyc erol: A new antifungal phosphocholine

The discovery of a new of antifungal agent, a glycosylated phosphatidylcholine, is reported, and the syntheses of the first two members of this series, (2S)-β-D-glucopyranos-1-yl-2-O-palmitoyl-3-O-phosphatidylcholinylglyc erol and (2R)-β-D-glucopyranos-1-yl-2-O-palmitoyl-3-O-phosphatidylcholinylglyc erol, are described. Their activities against the pathogenic fungi Candida albicans, Cryptococcus neoformans, and Aspergillus fumigatus are also reported.

Synthesis of phosphatidyl-α-glucosyl-diacylglycerol containing palmitic and oleic acid esters

The recently introduced 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane protecting group enabled us to synthesize a naturally occurring phosphatidyl-α-glucosyl-diacylglycerol via a phosphotriester intermediate.