115015-97-9

Usage

Derived from myoinositol

2,6-di-O-benzylmyoinositol is a chemical compound that is derived from myoinositol, a type of sugar alcohol.

Used in organic synthesis

2,6-di-O-benzylmyoinositol is often used in organic synthesis and as a building block in the production of various pharmaceuticals and natural products.

Created by benzylating the hydroxyl groups at positions 2 and 6

The compound is created by benzylating the hydroxyl groups at positions 2 and 6 of the myoinositol molecule.

Potential as a therapeutic agent

2,6-di-O-benzylmyoinositol has shown potential as a therapeutic agent for various medical conditions, including neurodegenerative diseases and diabetes.

Ongoing research

Research on 2,6-di-O-benzylmyoinositol is ongoing, and its potential applications continue to be explored.

InChI:InChI=1/C20H24O6/c21-15-16(22)19(25-11-13-7-3-1-4-8-13)18(24)20(17(15)23)26-12-14-9-5-2-6-10-14/h1-10,15-24H,11-12H2/t15?,16-,17+,18?,19-,20-/m1/s1

Upstream product

• 132741-45-8 (2S,3S)-1,4-Dioxa-spiro[4.5]decane-2,3-dicarboxylic acid methyl ester (1R,2S,3S,4R,5S,6R)-2,4,6-tris-benzoyloxy-3,5-bis-benzyloxy-cyclohexyl ester 
• 100-39-0 benzyl bromide 
• 114828-05-6 (1R,5S,6S,7R,8S,9R)-9-Allyloxy-2,4,10-trioxa-tricyclo[3.3.1.1^3,7]decane-6,8-diol 
• 117666-30-5 (+)-1,3,4,5-tetra-O-allyl-2,6-di-O-benzyl-myo-inositol 
• 114967-57-6 C₅₃H₅₆O₁₁ 
• 142387-49-3 (1S,2S,3R,4S,5R,6R)-3,5-Bis-benzyloxy-4,6-bis-[((E)-propenyl)oxy]-cyclohexane-1,2-diol 
• 142436-05-3 1D-2,6-di-O-benzyl-1,5-di-O-p-methoxybenzyl-myo-inositol 
• 187841-88-9 (1S,2S,3R,4R,5S,6R)-2,3,5-Tris-allyloxy-4,6-bis-benzyloxy-cyclohexanol 
• 108-05-4 vinyl acetate 
• 16749-97-6 racemic 2,4-di-O-benzyl-myo-inositol 
• 117666-30-5 (+/-)-1,3,4,5-tetra-O-allyl-2,6-di-O-benzyl-myo-inositol 
• 136118-83-7 (+/-)-2,6-di-O-benzyl-1,5-di-O-p-methoxybenzyl-myo-inositol 
• 98510-25-9 racemic 2,4-di-O-benzyl-myo-inositol 1,3,5-orthoformate 
• 98510-20-4 myo-Inositol orthoformate 

Downstream Products

• 115015-98-0 octabenzyl 1D-2,6-di-O-benzyl-myo-inositol 1,3,4,5-tetrakisphosphate 
• 115016-66-5 octa-ammonium salt of D-myo-inositol 1,3,4,5-tetrakisphosphate 
• 115015-97-9 (-)-1L-2,6-di-O-benzyl-myo-inositol 
• 210488-60-1 (-)-1L-5-O-acetyl-2,6-di-O-benzyl-myo-inositol 
• 142387-48-2 (+/-)-1,3-di-O-allyl-2,6-di-O-benzyl-4,5-O-isopropylidene-myo-inositol 
• 142387-45-9 (+/-)-2,6-di-O-benzyl-3,4-O-isopropylidene-1,5-di-O-p-methoxybenzyl-myo-inositol 
• 117666-33-8 Phosphorous acid dibenzyl ester (1R,2S,3S,4R,5R,6S)-2,6-bis-benzyloxy-3,4,5-tris-(bis-benzyloxy-phosphanyloxy)-cyclohexyl ester 
• 142387-42-6 C₄₃H₅₂O₁₂ 
• 142387-42-6 3,5-bis-(-)-ω-camphanate 1D-2,4-di-O-benzyl-1,6-O-isopropylidene-myo-inositol 
• 142387-51-7 4,5-bis-(-)-ω-camphanate 1D-1,3-di-O-allyl-2,6-di-O-benzyl-myo-inositol 
• 142387-47-1 C₅₆H₆₄O₁₄ 
• 142436-02-0 (3aR,4S,5R,6R,7R,7aR)-5,7-Bis-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-4,6-diol 
• 142436-10-0 (1S,2S,3R,4R,5S,6R)-3,5-Bis-allyloxy-4,6-bis-benzyloxy-cyclohexane-1,2-diol 
• 136091-44-6 (+/-)-1,3-Di-O-allyl-2,6-di-O-benzyl-myo-inositol 

Relevant academic research and scientific papers

An efficient route to optically active inositol derivatives via the resolution of myo-inositol 1,3,5-orthoformate: A short synthesis of D-myo-inositol-4-phosphate

An efficient method for the resolution of myo-inositol 1,3,5-orthoformate has been developed. The triol, 1 was converted to diastereomers via reaction with (S)-O-acetylmandeloyl chloride. Conditions were optimized for a diastereomeric ratio of 7:3. Both t

Clues from crystal structures pave the way to access chiral myo-inositol derived versatile synthons: Resolution of racemic 4?O?Allyl-myo-Inositol-1,3,5-orthoesters via corresponding dicamphanates by crystallization

Racemic 4-O-allyl-myo-inositol-1,3,5-orthoest-ers were resolved as the corresponding diastereomeric dicamphanates by crystallization from alcoholic solvents. Crystals of the two diastereomers of myo-inositol orthoacetate and one diastereomer each of myo-inositol orthoformate and myo-inositol orthobenzoate were obtained in >99% purity, on gram scale. The configuration of all these diastereomers was established by conversion to known chiral myo-inositol derivatives as well as by single crystal structure analysis. It is interesting to note that the procedures for the separation of diastereomeric myo-inositol orthoesters could be evolved due to the knowledge of crystal growth and crystal structures of inositol derivatives of comparable molecular structures. Due to the synthetic versatility of myo-inositol orthoesters, the methods described provide rapid and convenient access to a variety of chiral inositol derivatives with high synthetic potential.

Chiral desymmetrisation of myo-inositol 1,3,5-orthobenzoate gives rapid access to precursors for second messenger analogues

Chiral desymmetrisation of myo-inositol 1,3,5-orthobenzoate via the formation of diastereoisomeric bis[(1S)-(-)-camphanate] esters provides a convenient and fast route to precursors for biologically important inositol phosphates and lipids, and to synthet

Sulfonate protecting groups: Synthesis of D- and L-myo-inositol-1,3,4,5-tetrakisphosphate precursors by a novel silver(I) oxide-mediated O-alkylation of 2,4(6)-di-O-acyl-6(4)-O-sulfonyl-myo-inositol 1,3,5-orthoformate derivatives through intramolecular assistance of the sulfonyl group

Alkylation of racemic 2,4-di-O-acyl-6-O-sulfonyl-myo-inositol 1,3,5-orthoformates mediated by silver(I) oxide affords the corresponding racemic 2,4-di-O-alkyl-6-O-sulfonyl-myo-inositol 1,3,5-orthoformates in good yields. Control experiments suggest that these unusual reactions are due to intramolecular assistance by the sulfonyl group. O-Alkylation reactions of myo-inositol 1,3,5-orthoformate derivatives provide a new route for the synthesis of important ether derivatives of myo-inositol, which are intermediates for the preparation of phosphoinositols. The utility of this method is demonstrated by the preparation of D- and L-2,4-di-O-benzyl-myo-inositols, which were obtained by benzylation of 2,4-di-O-benzoyl-6-O-camphorsulfonyl-myo-inositol 1,3,5-orthoformate and 2,6-di-O-benzoyl-4-O-camphorsulfonyl-myo-inositol 1,3,5-orthoformate. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

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.

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.

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.

The preparation of racemic and enantiomerically pure myo-inositol derivatives as intermediates for the synthesis of phosphatidylinositol 3-, 3,4-bis-, and 3,4,5-tris-phosphates and for the synthesis of analogues of 1D-myo-inositol 1,3,4,5-tetrakisphosphat

Details of the products obtained by the tin-mediated allylation and benzylation of 1,2-O-isopropylidene-myo-inositol, which were previously described in a preliminary communication, are provided here. Some of the products from these reactions, particularl

The preparation and phosphorylation of 2,5- and 1D-2,6-di-O-benzyl-myo-inositol

1,3,4,6-Tetra-O-allyl-myo-inositol was converted into the 2,5-di-O-benzyl- and 2,5-di-O-p-methoxybenzyl ethers, and the products were deallylated to give the 2,5-di-O-benzyl (and p-methoxybenzyl) ethers of myo-inositol, which were converted into the mono-

An efficient chemoenzymic access to optically active myo-inositol polyphosphates

The 1,4,5-tris-, 1,3,4-tris-, and 1,3,4,5-tetrakis-phosphates of 1D-myo-inositol have been prepared in their enantiomerically pure forms from the two enantiomers of 1,2:5,6-di-O-cyclohexylidene-myo-inositol. A facile enzymic preparation is also described