124684-96-4

Upstream product

• 124778-85-4 3,4,5,6-tetra-O-benzyl-1-O-prop-1-enyl-2-O-(2',3',4',6'-tetra-O-benzyl-α-D-mannopyranosyl)-D-myo-inositol 
• 124684-95-3 1-O-allyl-3,4,5,6-tetra-O-benzyl-2-O-(2',3',4',6'-tetra-O-benzyl-α-D-mannopyranosyl)-D-myo-inositol 
• 170900-81-9 3,4,5,6-tetra-O-benzyl-1-O-p-methoxybenzyl-D-myo-inositol 
• 148171-71-5 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl dimethyl phosphite 
• 100-39-0 benzyl bromide 
• 169106-94-9 2-O-acetyl-3,4,6-tri-O-benzyl-α/β-D-mannopyranosyl fluoride 

Downstream Products

• 24558-77-8 3,4,5,6-tetra-O-benzyl inositol 
• 1034620-22-8 3,4,5,6-tetra-O-benzyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-1-O-(1-O-hexadecanoyl-2-O-hexadecyl-sn-glycero-3-benzylphosphoryl)-D-myo-inositol 
• 1092959-36-8 triethylammonium 1-O-(6-(S-benzyl)thiohexylphosphonato)-2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-3,4,5,6-tetra-O-benzyl-D-myo-inositol 
• 124684-97-5 3,4,5,6-tetra-O-benzyl-2-O-(2',3',4',6'-tetra-O-benzyl-α-D-mannopyranosyl)-1-O-(1,2-di-O-palmitoyl-sn-glycero)-D-myo-inositol benzylphosphate 

Relevant academic research and scientific papers

CHEMICAL SYNTHESIS OF PHOSPHATIDYLINOSITOL MANNOSIDE GLYCANS FROM MYCOBACTERIUM TUBERCULOSIS

The efficient synthesis of phosphatidylinositol mono- to hexa-mannoside (PIM1 to PIM6) is reported. The invention relates to these phosphatidylinositol mono- to hexa-mannosides carrying a linker and a reactive functional group, e.g. the sulfhydryl group, a protein, a fluorescent probe, or a solid phase. The invention further relates to vaccines comprising the PIMs linked to a carrier protein or an antigen

Chemical synthesis of all phosphatidylinositol mannoside (PIM) glycans from Mycobacterium tuberculosis

The emergence of multidrug-resistant tuberculosis (TB) and problems with the BCG tuberculosis vaccine to protect humans against TB have prompted investigations into alternative approaches to combat this disease by exploring novel bacterial drug targets and vaccines. Phosphatidylinositol mannosides (PIMs) are biologically important glycoconjugates and represent common essential precursors of more complex mycobacterial cell wall glycolipids including lipomannan (LM), lipoarabinomannan (LAM), and mannan capped lipoarabinomannan (ManLAM). Synthetic PIMs constitute important biochemical tools to elucidate the biosynthesis of this class of molecules, to reveal PIM interactions with host cells, and to investigate the function of PIMs as potential antigens and/or adjuvants for vaccine development. Here, we report the efficient synthesis of all PIMs including phosphatidylinositol (Pl) and phosphatidylinositol mono- to hexa-mannoside (PIM1 to PIM6). Robust synthetic protocols were developed for utilizing bicyclic and tricyclic orthoesters as well as mannosyl phosphates as glycosylating agents. Each synthetic PIM was equipped with a thiol-linker for immobilization on surfaces and carrier proteins for biological and immunological studies. The synthetic PIMs were immobilized on microarray slides to elucidate differences in binding to the dendritic cell specific intercellular adhesion molecule-grabbing nonintegrin (DC-SIGN) receptor. Synthetic PIMs served as immune stimulators during immunization experiments in C57BL/6 mice when coupled to the model antigen keyholelimpet hemocyanin (KLH).

Phosphatidylinositol mannosides: Synthesis and suppression of allergic airway disease

Phosphatidylinositol mannoside (PIM) extracts from mycobacteria have been shown previously to suppress allergic airway inflammation in mice. To help determine the structural requirements for activity, PIM12 (1), PIM16 (2) and PIM2 (3

The synthesis of 1-O-(2-N-stearoyl-D-erythro-sphinganine-1-phosphoryl)-2-O-(α-D-mannopyranosyl-D-myo-inositol: a fragment of the naturally occurring inositol-containing glycophosphosphingolipids

Chiral mannosylinositol containing sphingophospholipid was synthesized from D-erythro ceramide and optically active mannosyl-myo-inositol with the use of phosphite triester coupling procedure.The optical resolution of racemic 3,4,5,6-tetra-O-benzyl-myo-in

SYNTHESIS OF 1-O-(1,2-DI-O-PALMITOYL-SN-GLYCERO-3-PHOSPHORYL)-2-O-α-D-MANNOPYRANOSYL-D-MYO-INOSITOL: A FRAGMENT OF MYCOBACTERIAL PHOSPHOLIPIDS

Optically active and partially benzylated 1-O-(2-O-α-D-mannopyranosyl)-D-myo-inositol was coupled, via a trivalent phosphorus method, with 1,2-di-O-palmitoyl-sn-glycerol.Oxidation of the intermediate phosphite-triester, and subsequent removal of the P(V)-