853308-55-1

Upstream product

• 14218-11-2 2,3,4,6-Tetra-O-benzoyl-α-D-mannopyranosyl bromide 
• 107-18-6 allyl alcohol 
• 127305-34-4 2,3,4,6-tetra-O-Bz-α-D-mannopyranosyl bromide 

Downstream Products

• 1175007-08-5 C₁₆H₂₀O₇ 
• 1352427-79-2 (2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-2,3,4,6-tetra-O-benzoyl-β-D-mannopyranoside 
• 627466-98-2 2,3,4,6-tetra-O-benzoyl-α,β-D-mannospyranose 

Relevant academic research and scientific papers

Polymerization of mannosyl tricyclic orthoesters for the synthesis of α(1-6) mannopyranan-the backbone of lipomannan

Tuberculosis (TB) remains a major health problem worldwide. Understanding the interactions between the surface components of Mycobacterium tuberculosis (Mtb), the main causative agent of TB, with host immune response will be critical for developments of e

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).

Automated synthesis of lipomannan backbone α(1-6) oligomannoside via glycosyl phosphates: Glycosyl tricyclic orthoesters revisited

Glycosyl tricyclic orthoesters provide a versatile basis for the efficient generation of glycosyl phosphates, which are used in the automated synthesis of lipomannan backbone α(1-6) hexa-mannoside. The Royal Society of Chemistry.

Ionic liquid [bmim]PF6-mediated synthesis of 1,2-orthoesters of carbohydrates and the glycosidation reactions of 4-pentenyl orthoesters

A facile synthesis of the 1,2-orthoesters of carbohydrates in the ionic liquid [bmim]PF6 without a quaternary ammonium salt like tetrabutylammonium iodide, is described. The glycosidation reactions of 4-pentenyl orthoesters (NPOEs) with differe

A facile and eco-friendly method for the synthesis of 1,2-orthoesters of carbohydrates in ionic liquid

A facile method for the synthesis of 1,2-orthoesters of carbohydrates in ionic liquid [bmim]PF6 is described. The method described herein is simpler, eco-friendly and avoids the addition of quaternary ammonium salts as promoters.