28140-43-4

Upstream product

• 26276-99-3 rac-1,4,5,6-tetra-O-benzyl-myo-inositol 
• 74-88-4 methyl iodide 
• 6691-27-6 (+/-)-cis-1,2-O-cyclohexylidene-3,4,5,6-tetrakis-O-benzyl myo-inositol 
• 111392-23-5 C₃₈H₄₂O₆ 
• 111392-22-4 C₃₈H₄₂O₆ 
• 170900-81-9 3,4,5,6-tetra-O-benzyl-1-O-p-methoxybenzyl-D-myo-inositol 
• 24558-77-8 3,4,5,6-tetra-O-benzyl inositol 

Downstream Products

• 1054626-90-2 Hexanoic acid (R)-1-hexanoyloxymethyl-2-[((1S,2R,3S,4S,5R,6R)-2,3,4,5-tetrahydroxy-6-methoxy-cyclohexyloxy)-(2-trimethylsilanyl-ethoxy)-phosphoryloxy]-ethyl ester 
• 183447-89-4 Hexanoic acid (R)-1-hexanoyloxymethyl-2-[((1R,2R,3S,4R,5S,6R)-2,3,4,5-tetrakis-benzyloxy-6-methoxy-cyclohexyloxy)-(2-trimethylsilanyl-ethoxy)-phosphoryloxy]-ethyl ester 
• 16749-93-2 rac.-2,4,5,6-Tetra-O-acetyl-1-O-benzyl-3-O-methoxy-myoinosit 

Relevant academic research and scientific papers

Synthesis and Kinetic Evaluation of Inhibitors of the Phosphatidylinositol-Specific Phospholipase C from Bacillus cereus

Substrate analogues of phosphatidylinositol (1) were synthesized and evaluated as potential inhibitors of the bacterial phosphatidylinositol-specific phospholipase C (PI-PLC) from Bacillus cereus.The chiral analogues of the water-soluble phospholipid substrate 5 were designed to probe the effects of varying the inositol C-2 hydroxyl group, which generally believed to serve as the nucleophile in the first step of the hydrolysis of phosphatidylinositols by PI-PLC.In the analogues 6-9, the C-2 hydroxyl group on the inositol ring of the phosphatidylinositol derivatives was rationally altered in several ways.Inversion of the stereochemistry at C-2 of the inositol ring led to the scyllo derivative 6.The inositol C-2 hydroxy group was replaced with inversion by a fluorine to produce the scyllo-fluoro inositol 7 and with a hydrogen atom to furnish the 2-deoxy compound 8.The C-2 hydroxyl group was O-methylated to prepare the methoxy derivative 9.The natural inositol configuration at C-2 was retained in the nonhydrolyzable phosphorodithioate analogue 10.The inhibition of PI-PLC by each of these analogues was then analyzed in a continuous assay using D-myo-inositol 1-(4-nitrophenyl phosphate) (25) as a chromogenic substrate.The kinetic parameters for each of these phosphatidylinositol derivatives were determined, and each was found to be a competitive inhibitor with Ki's as follows: 6, 0.2 mM; 10, 0.6 mM; 8, 2.6 mM; 9, 6.6 mM; and 7, 8.8 mM.This study further establishes that the hydrolysis of phosphatidylinositol analogues by bacterial PI-PLC requires not only the presence of a C-2 hydroxyl group on the inositol ring, but the stereochemistry at this position must also correspond to the natural myo-configuration.For future inhibitor design, it is perhaps noteworthy that the best inhibitors 6 and 10 each possess a hydroxyl group at the 2-position.Several of the inhibitors identified in this study are now being used to obtain crystallographic information for an enzyme-inhibitor complex to gain further insights regarding the mechanism of hydrolysis of phosphatidylinositides by this PI-PLC.

The Allyl Group for Protection in Carbohydrate Chemistry. Part 18. Allyl and Benzyl Ethers of myo-Inositol. Intermediates for the Synthesis of myo-Inositol Triphosphates

Racemic 1,2:4,5-di-O-isopropylidene-myo-inositol was converted into racemic 1,2,4-tri-O-benzyl-myo-inositol, 1,2,4-tri-O-p-methoxybenzyl-myo-inositol and 2,4,5-tri-O-benzyl-myo-inositol using allyl groups for 'temporary' protection.The benzyl ethers are required as intermediates for the synthesis of the 'second messenger', inositol 1,4,5-triphosphate and its metabolite, inositol 1,3,4-triphosphate. 1,2,3,4-Tetra-O-benzyl-myo-inositol, and its two monoallyl and monoprop-1-enyl ethers, were also prepared as model compounds for phosphorylation studies of the vicinal 5,6-diol system which occurs in 1,2,4-tri-O-benzyl-myo-inositol.