149713-85-9

Upstream product

• 136118-83-7 (+/-)-2,6-di-O-benzyl-1,5-di-O-p-methoxybenzyl-myo-inositol 
• 87-89-8 D-myo-inositol 
• 114828-05-6 4/6-O-allyl-myo-inositol 1,3 5-monoorthoformate 
• 100-39-0 benzyl bromide 
• 98510-22-6 (1R,3S,5S,6R,7S,8S,9S)-9-<(tert-butyl)dimethylsilyloxy>-2,4,10-tri-oxatricyclo<3.3.1.1^3,7>decane-6,8-diol 
• 6404-82-6 (+/-)-1,2-O-isopropylidene-myo-inositol 
• 98510-25-9 meso-4,6-di-O-benzyl-D-myo-inositol-1,3,5-O-orthoformate 
• 98510-24-8 (1R,3S,5S,6R,7S,8S,9S)-6,8-bis(benzyloxy)-9-<(tert-butyl)dimethylsilyloxy>-2,4,10-tri-oxatricyclo<3.3.1.1^3,7>decane 
• 126960-07-4 1,3,4,5-tetra-O-benzoyl-myo-inositol 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 136986-14-6 (+/-)-1,3,4,5-tetra-O-allyl-myo-inositol 

Downstream Products

• 127996-98-9 dipalmitoyl PtdIns₄P 
• 1449380-47-5 C₃₄H₃₁BrO₈ 
• 1449380-43-1 (1R,2S,3S,4S,5R,6S)-3-O-benzoyl-4,6-di-O-benzyl-myo-inositol 
• 785817-89-2 (1S,2R,3R,4R,5S,6R)-3-O-benzoyl-4,6-di-O-benzyl-myo-inositol 
• 159802-94-5 1D-1-O-acetyl-4,6-di-O-benzyl-2,3-O-isopropylidene-myo-inositol 
• 160401-89-8 1L-4,6-di-O-benzyl-1,2-O-isopropylidene-myo-inositol 
• 15421-51-9 myo-inositol 1-phosphate 
• 291527-84-9 1-O-(4'-methoxybenzyl)-2,3,4,6-tetra-O-benzyl-myo-inositol-5-(dibenzyl phosphate) 
• 291527-78-1 Phosphoric acid dibenzyl ester (1S,2R,3R,4S,5R,6S)-2,4-bis-benzyloxy-3-(bis-benzyloxy-phosphoryloxy)-5,6-dihydroxy-cyclohexyl ester 

Relevant academic research and scientific papers

Development of isotope-enriched phosphatidylinositol-4- And 5-phosphate cellular mass spectrometry probes

Synthetic phosphatidylinositol phosphate (PtdInsPn) derivatives play a pivotal role in broadening our understanding of PtdInsPnmetabolism. However, the development of such tools is reliant on efficient enantioselective and regioselective synthetic strategies. Here we report the development of a divergent synthetic route applicable to the synthesis of deuterated PtdIns4Pand PtdIns5Pderivatives. The synthetic strategy developed involves a key enzymatic desymmetrisation step using Lipozyme TL-IM. In addition, we optimised the large-scale synthesis of deuteratedmyo-inositol, allowing for the preparation of a series of saturated and unsaturated deuterated PtdIns4Pand PtdIns5Pderivatives. Experiments in MCF7 cells demonstrated that these deuterated probes enable quantification of the corresponding endogenous phospholipids in a cellular setting. Overall, these deuterated probes will be powerful tools to help improve our understanding of the role played by PtdInsPnin physiology and disease.

Desymmetrization of 4,6-diprotected myo-inositol

The asymmetric desymmetrization of 4,6-diprotected myo-inositol derivatives was achieved by using a bifunctional, readily available nucleophilic catalyst. The orthogonally protected products were obtained in 80-99% yield with 90-99% ee. Such structures serve as potential enantiopure building blocks for the synthesis of myo-inositol phosphates.

Conformational study of the natural iron chelator myo-inositol 1,2,3-trisphosphate using restrained/flexible analogues and computational analysis

Myo-Inositol 1,2,3-trisphosphate [Ins(1,2,3)P3], a component in mammalian cells, possesses the correct chemical properties of an intracellular iron transit ligand. Here we have examined the conformation of the Ins(1,2,3)P3-Fe3+ complex. The synthesis and antioxidant properties of 4,6-carbonate-myo-inositol 1,2,3,5-tetrakisphosphate [4,6-carbonate Ins(1,2,3,5)P4], which is locked in the unstable penta-axial chair conformation and 1,2,3-trisphosphoglycerol, a flexible acyclic analogue of Ins(1,2,3)P3, are reported. 4,6-Carbonate Ins(1,2,3,5)P4 caused complete inhibition of iron-catalysed hydroxyl radical (HO?) formation at 100 μM, thereby resembling Ins(1,2,3)P3 and supporting a penta-axial chair binding conformation. In contrast, 1,2,3-trisphosphoglycerol was shown to have incomplete antioxidant properties. In support of experimental observations, we have applied high-level density functional calculations to the binding of Ins(1,2,3)P3 to iron. This study provides evidence that Fe3+ binds tightly to the less stable penta-axial conformation of Ins(1,2,3)P3 using terminal and bridging phosphate oxygens, thought to also contain a tightly bound water molecule or hydroxyl ligand in the complex.

Sulfonate protecting groups. Regioselective sulfonylation of myo-inositol orthoesters-improved synthesis of precursors of D- and L-myo-inositol 1,3,4,5-tetrakisphosphate, myo-inositol 1,3,4,5,6-pentakisphosphate and related derivatives.

The regioselectivity of sulfonylation of myo-inositol orthoesters was controlled by the use of different bases to obtain the desired sulfonate. Monosulfonylation of myo-inositol orthoesters in the presence of one equivalent of sodium hydride or triethylamine resulted in the sulfonylation of the 4-hydroxyl group. The use of pyridine as a base for the same reaction resulted in sulfonylation of the 2-hydroxyl group. Disulfonylation of these orthoesters in the presence of excess sodium hydride yielded the 4,6-di-O-sulfonylated orthoesters. However, the use of triethylamine or pyridine instead of sodium hydride yielded the 2,4-di-O-sulfonylated orthoester. Sulfonylated derivatives of myo-inositol orthoesters were stable to conditions of O-alkylation but were cleaved using magnesium/methanol or sodium methoxide in methanol to regenerate the corresponding myo-inositol orthoester derivative. These new methods of protection-deprotection have been used: (i) for the efficient synthesis of enantiomers of 2,4-di-O-benzyl-myo-inositol, which are precursors for the synthesis of D- and L-myo-inositol 1,3,4,5-tetrakisphosphate; (ii) for the preparation of 2-O-benzyl-myo-inositol which is a precursor for the preparation of myo-inositol 1,3,4,5,6-pentakisphosphate.

Convenient synthesis of 4,6-di-O-benzyl-myo-inositol and myo-inositol 1,3,5-orthoesters

Convenient high yielding methods for the preparation of 4,6-di-O-benzyl-myo-inositol, myo-inositol 1,3,5-orthoformate and myo-inositol 1,3,5-orthoacetate, without involving chromatography are described. Myo-inositol was converted to racemic 2,4-di-O-benzoyl-myo-inositol 1,3,5-orthoformate by successive treatment with triethyl orthoformate and benzoyl chloride. The dibenzoate obtained on benzylation with benzyl bromide and silver(I) oxide gave 2-O-benzoyl-4,6-di-O-benzyl-myo-inositol 1,3,5-orthoformate. Deprotection of the benzoate and the orthoformate with isobutylamine and aqueous trifluoroacetic acid, respectively gave 4,6-di-O-benzyl-myo-inositol in an overall yield of 67%. Myo-inositol orthoformate and orthoacetate were prepared and isolated as their tribenzoates. The free orthoesters were regenerated by deprotection of the benzoates by aminolysis with isobutylamine.

Sulfonate protecting groups. Regioselective O-sulfonylation of myo-inositol orthoesters

Sulfonylation of myo-inositol 1,3,5-orthoesters with alkyl or aryl sulfonyl chlorides in the presence of sodium hydride gives the corresponding 4,6-di-O-sulfonates in good yields. These sulfonates can be cleaved with magnesium in methanol to generate the free myo-inositol derivative. This methodology was used for the preparation of racemic 2,4-di-O-benzyl-myo-inositol and 2-O-benzyl-myo-inositol, which are precursors for some phosphoinositols.

Concise syntheses of L-α-phosphatidyl-D-myo-inositol 3-phosphate (3- PIP), 5-phosphate (5-PIP), and 3,5-bisphosphate (3,5-PIP2)

Highly efficient, asymmetric total syntheses of the title phospholipids as well as short chain and crosslinkable aminoether analogs were achieved in five to seven steps from a readily available myo-inositol derivative. (C) 2000 Elsevier Science Ltd.

Preparation of L-α-phosphatidyl-D-myo-inositol 3-phosphate (3-PIP) and 3,5-biphosphate (3,5-PIP2)

Practical, asymmetric total syntheses of the title phospholipids from a readily available myo-inositol derivative as well as short chain and cross-linkable aminoether analogues are described. (C) 2000 Elsevier Science Ltd. All rights reserved.

Chemo-enzymatic synthesis of both enantiomers of myo-inositol 1,3,4,5-tetrakisphosphate

D-Ins(1,3,4,5)P4 and unnatural L-Ins(1,3,4,5)P4 were prepared in gram-quantities from D- and L-2,6-di-O-benzyl-myo-inositol by a chemical phosphorylation and deprotection step in high yield and purity without extensive purification.

Racemic 2,4-di-O-benzoyl-myo-inositol 1,3,5-orthoformate: A versatile intermediate for the preparation of myo-inositol phosphates

The versatility of racemic 2,4-di-O-benzoyl-myo-inositol 1,3,5- orthoformate as an intermediate for the preparation of protected myo- inositol derivatives is demonstrated. Procedures described provide simple access to several protected myo-inositol derivatives which are intermediates for the preparation of myo-inositol phosphates and racemic ononitol.