137793-99-8

Upstream product

• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 2595-06-4 methyl 2,3,4-tri-O-benzyl-6-O-trityl-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 1079205-73-4 C₃₇H₅₂O₆Si 
• 18311-26-7 methyl 6-O-trityl-α-D-glucopyranoside 
• 492-62-6 alpha-D-glucopyranose 
• 137793-90-9 (Z)-methyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-gluco-hex-5-enopyranoside 
• 137793-91-0 (E)-methyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-gluco-hex-5-enopyranoside 
• 83051-88-1 methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 137793-96-5 (1R,2R,3S,4R,5S)-3,4,5-tribenzyloxy-2-hydroxy-6-oxocyclohexyl acetate 

Downstream Products

• 131233-69-7 3,4,5-tri-O-benzyl-D-myo-inositol 
• 273934-62-6 1-O-acetyl-3,4,5-tri-O-benzyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-D-myo-inositol 
• 202845-40-7 1-((1S,2S,3S,4R,5S,6S)-2-Allyloxy-3,4,5,6-tetrakis-benzyloxy-cyclohexyloxymethyl)-4-methoxy-benzene 
• 132437-54-8 1-O-allyl-2,3,4,5-tetra-O-benzyl-D-myo-inositol 
• 64681-28-3 D-1-O-allyl-3,4,5,6-tetra-O-benzyl-myo-inositol 
• 132437-55-9 1-O-allyl-2,3,4,5,6-penta-O-benzyl-D-myo-inositol 
• 87-89-8 D-myo-inositol 
• 202845-42-9 1-O-allyl-3,4,5-tri-O-benzyl-D-myo-inositol 
• 883878-67-9 (2-O-benzoyl-3,4-di-O-benzyl-6-O-levulinoyl-α-D-mannopyranosyl)-(1->6)-1-O-allyl-3,4,5-tri-O-benzyl-2-O-naphthylmethyl-D-myo-inositol 
• 883878-66-8 (2-O-benzoyl-3,4-di-O-benzyl-α-D-mannopyranosyl)-(1->6)-1-O-allyl-3,4,5-tri-O-benzyl-2-O-naphthylmethyl-D-myo-inositol 
• 883878-68-0 (2-O-benzoyl-3,4-di-O-benzyl-6-O-levulinoyl-α-D-mannopyranosyl)-(1->6)-1-O-allyl-3,4,5-tri-O-benzyl-D-myo-inositol 
• 883878-65-7 1-O-allyl-3,4,5-tri-O-benzyl-2-O-naphthylmethyl-D-myo-inositol 

Relevant academic research and scientific papers

A five-component one-pot synthesis of phosphatidylinositol pentamannoside (PIM5)

A practical and efficient synthesis of phosphatidylinositol pentamannoside (PIM5) was achieved based on a five-component one-pot sequential glycosylation protocol with exclusive regio- and stereo-selectivity. Two regioselective sequential glycosylations on inositol and p-tolyl thioglycosides as the sole type of building blocks made this protocol to avoid the tedious protective group manipulations. This synthetic strategy provides access to other important glycolipids with similar structures.

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).

Novel synthesis of enantiomerically pure natural inositols and their diastereoisomers

The various inositol polyphosphates have been found to trigger many important biological processes. Although the knowledge of this phosphoinositide signaling system has been discovered in the past 10 years, many factors remain unclear. For this reason, there is an increased demand for supplies of D-myo-inositol and particularly of novel analogues to investigate these biological mechanisms in more detail. Herein, we report the efficient syntheses of all diastereoisomers of inositol starting with 6-O-acetyl-5-enopyranosides. Conversion of 6-O-acetyl-5-enopyranosides into the corresponding substituted cyclohexanones (Ferrier-II rearrangement) was found to proceed efficiently with a catalytic amount of palladium dichloride. Stereoselective reduction of β-hydroxy ketones obtained provided the precursors to all inositol diastereoisomers in good to excellent yields and with high stereoselectivities. Good accessibility of these enantiomerically pure inositol diastereoisomers results in the efficient syntheses of D-myo-inositol 1,4,5-trisphosphate and D-myo-inositol 1,3,4,5-tetrakisphosphate.

13C Labelling and electrospray mass spectrometry reveal a de novo route for inositol biosynthesis in Leishmania donovani parasite

In this paper we provide evidence for the presence of a de now route for myo-inositol biosynthesis in the protozoan parasite Leishmania donovani, by the application of 13C labelling and electrospray ionisation mass spectrometry (ESMS). For this myo-[1-13C]inositol is prepared from D-[6-13C]glucose and biosynthetically incorporated in the parasite promastigote cell culture. Biosynthetic phosphatidylinositol (PI) and its hydrolysis products glycero-PI and inositol are analysed by ESMS and the isotopomeric ratio determined. The incorporation experiments show substantial isotopic dilution, indicating the presence of myo-inositol 1-phosphate synthase (MIP synthase) enzyme in the parasite; this is further confirmed by incorporation of D-[6-13C]glucose in the parasite phosphatidylinositol. The Royal Society of Chemistry 2000.

Novel synthesis of enantiomerically pure natural inositols and their diastereomers

A novel synthesis of all stereoisomers of natural inositols has been developed. The key strategy is the stereoselective reduction of substituted β-hydroxy cyclohexanones which are prepared from a variety of 6-O-acetyl 5- enopyranosides via Ferrier-II reaction catalyzed by palladium chloride. The utility of this approach is demonstrated by the synthesis of D-myo-inositol 1,4,5-tris(phosphate)(IP3).

Ready routes to key myo-inositol component of GPIs employing microbial arene oxidation or Ferrier reaction

Microbial arene oxidation or Ferrier reaction of enol acetates provides versatile complementary routes that greatly facilitate preparation of inositol synthon(s) for GPI assembly.