114828-08-9

Basic information

• Product Name: (1R,2S,3r,4R,5S,6s)-2,4,6-tris(benzyloxy)cyclohexane-1,3,5-triol
• Synonyms: (1R,2S,3r,4R,5S,6s)-2,4,6-tris(benzyloxy)cyclohexane-1,3,5-triol;Myo-Inositol, 2,4,6-tris-O-(phenylMethyl)-;2,4,6-Tri-O-benzyl-myo-inositol
• CAS NO: 114828-08-9
• Molecular Formula: C₂₇H₃₀O₆
• Molecular Weight: 451
• EINECS: -0
• Mol File: 114828-08-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1R,2S,3r,4R,5S,6s)-2,4,6-tris(benzyloxy)cyclohexane-1,3,5-triol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S,3r,4R,5S,6s)-2,4,6-tris(benzyloxy)cyclohexane-1,3,5-triol(114828-08-9)
• EPA Substance Registry System: (1R,2S,3r,4R,5S,6s)-2,4,6-tris(benzyloxy)cyclohexane-1,3,5-triol(114828-08-9)

Safety Data

• Hazardous Substances Data: 114828-08-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(1R,2S,3r,4R,5S,6s)-2,4,6-tris(benzyloxy)cyclohexane-1,3,5-triol serves as a key intermediate in organic synthesis, providing a versatile platform for the creation of various complex organic molecules. Its unique structure allows for multiple points of functionalization, making it a valuable component in the synthesis of a wide range of compounds.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (1R,2S,3r,4R,5S,6s)-2,4,6-tris(benzyloxy)cyclohexane-1,3,5-triol is employed as a building block for the design and synthesis of pharmaceuticals. Its presence of multiple hydroxyl and benzyloxy groups facilitates the attachment of various functional groups, enabling the development of new drugs with improved pharmacological properties.
Used in the Synthesis of Biologically Active Molecules:
(1R,2S,3r,4R,5S,6s)-2,4,6-tris(benzyloxy)cyclohexane-1,3,5-triol is also utilized in the synthesis of biologically active molecules, such as natural products and bioactive compounds. Its structural features make it an ideal candidate for the development of molecules with potential therapeutic applications, including those targeting specific diseases or biological processes.
Used in Pharmaceutical Industry:
Within the pharmaceutical industry, (1R,2S,3r,4R,5S,6s)-2,4,6-tris(benzyloxy)cyclohexane-1,3,5-triol is used as a precursor for the production of various drugs. Its unique structure and functional groups contribute to the development of innovative medications with enhanced efficacy and selectivity, ultimately benefiting patients and advancing healthcare.

Upstream product

• 114847-11-9 meso-2,4,6-tri-O-benzyl-D-myo-inositol-1,3,5-O-orthoformate 
• 120268-33-9 4/6-O-benzyl-myo-inositol 1,3,5-monoorthoformate 
• 100-39-0 benzyl bromide 
• 227177-05-1 (±)-2,4,6-tri-O-benzyl-1,5-O-ethyldiene myo-inositol 
• 98510-20-4 myo-Inositol orthoformate 
• 87-89-8 D-myo-inositol 
• 227177-02-8 (1R*,3R*,5S*,6R*,7R*,8R*,9R*)-6,8,9-tris(benzyloxy)-7-<(4'-methoxyphenyl)methoxy>-3-methyl-2,4-dioxabicyclo<3.3.1>nonane 
• 227177-05-1 2,4,6-tri-O-benzyl-1,5-O-ethylidene-DL-myo-inositol 

Downstream Products

• 131147-14-3 1,2,4,6-tetra-O-benzyl-DL-myo-inositol 
• 30694-52-1 1,2,3,4,6-Penta(O-benzyl)-myo-inositol 
• 1173293-47-4 C₇₄H₇₅O₁₄P 
• 132747-00-3 D(+)-1,2,4,6-Tetra-O-benzyl-myo-inositol 
• 132746-98-6 L(-)-1,2,4,6-Tetra-O-benzyl-myo-inositol 
• 132662-61-4 (1R,4S)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1S,2R,3R,4S,5S,6R)-2,3,4,6-tetrakis-benzyloxy-5-hydroxy-cyclohexyl ester 
• 132662-61-4 (1R,4S)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1R,2S,3S,4R,5R,6S)-2,3,4,6-tetrakis-benzyloxy-5-hydroxy-cyclohexyl ester 
• 132662-63-6 Sulfamic acid (1S,2R,3R,4R,5R,6R)-2,3,4,6-tetrahydroxy-5-sulfamoyloxy-cyclohexyl ester 
• 143538-51-6 2,4,6-O-tribenzyl myo-inositol-1,3,5-O-thiophosphate 
• 167819-57-0 C₃₉H₅₁O₁₈P₃ 
• 130515-75-2 1,3,5-Tri-O-benzoyl-myo-inositol 

Relevant articles and documents

Total syntheses of cyclitol based natural products from myo-inositol: brahol and pinpollitol

Inositol and their derivatives are important class of biologically active natural products. Among the nine theoretically possible inositols, six are known to occur in nature. Interestingly one or more methyl ethers of these inositols have been isolated fr

Establishment of the structure of pinpollitol by total synthesis of the proposed putative structures

Proposed structures of pinpollitol, namely 1,4-di-O-methyl-chiro-inositol and 1,3-di-O-methyl-chiro-inositol, have been synthesized from myo-inositol. Racemic 1,4-di-O-methyl-chiro-inositol has been synthesized from the readily available 1,2:4,5-di-O-isop

Synthesis and in vitro anticancer activity evaluation of novel bioreversible phosphate inositol derivatives

The chemistry and biology of phosphorylated inositols have become intense areas of research during the last two decades due to their involvement in various cellular signaling processes. However, the metabolic instability by phosphatases or kinases and poo

General synthesis of 3-phosphorylated mj'o-inositol phospholipids and derivatives

The D-3-phosphorylated wyo-inositol phospholipids PtdIns(3)P, PtdIns(3,4)P2, PtdIns(3,4,5)P3 and PtdIns(3,5)P2 were synthesised from /yo-inositol orthoformate 8. Key transformations included the regioselective DIBAL- and trimethylaluminium-mediated cleavages of wiyo-inositol orthoformate intermediates and a resolution-protection protocol using the camphor acetals 17. The final reductive debenzylation was effected with Pearlman's catalyst [Pd(OH)J in the presence of sodium hydrogen carbonate. The biological properties of the phospholipids were evaluated against various protein kinases (PKB and PDK-1) in which they played an important activation role.

Syntheses of myo-inositol-1,2,3,5- and 2,4,5,6-tetrakisphosphates, unusual inhibitors of myo-inositol-1,4,5-trisphosphae 3-kinase

D-myo-Inositol 1,4,5-trisphosphate [D-I(1,4,5)P3], a calcium mobilizing second messenger, is converted to D-I(1,3,4,5)P4 by D-I(1,4,5)P3-3-kinase. Efficient syntheses of I(1,2,3,5)P4 (2) and I(2,4,5,6)P4 (3), novel 3-kinase inhibitors, are reported.

Membrane-permeant esters of inositol polyphosphates, chemical syntheses and biological applications

Membrane-permeant derivatives of inositol polyphosphates are useful tools for biological studies. Racemic 2,3,6-tri-O-butyryl-myo-inositol 1,4,5-trisphosphate hexakis(acetoxymethyl) ester(Bt3IP3/AM), myo-inositol 1,4,5-trisphosphate hexakis(acetoxymethyl) ester (IP3/AM), hexakis(propionyloxymethyl) ester (IP3/PM) and hexakis(butyryloxymethyl) ester (IP3/BM) were therefore synthesized. Whereas extracellular application of up to 200 μM of Bt3IP3/AM or IP3/AM to 1321N1 astrocytoma cells failed to mobilize internal calcium, IP3/PM and IP3/BM released internal calcium at concentrations as low os 20 μM and 2 μM, respectively.

Practical divergent synthesis of all possible regioisomers of myo-inositol trisphosphates

The synthesis of all possible 12 regioisomers of IP3, some of which are implicated as second messengers in cellular signalling, is accomplished from myo-inositol via its tribenzoate derivatives (IBz3) as the key intermediates.

STUDIES ON ORGANOPHOSPHORUS COMPOUNDS 58. SYNTHESIS OF myo-INOSITOL-1,3,5-O-PHOSPHATE AS A NEW TYPE OF CAGE-PHOSPHATE

A new type of a cage-phosphate with resemblance to the adamantane structure namely myo-inositol-1,2,5-O-phosphate was synthesized by debenzylation of 2,4,6-O-tribenzyl-myo-inositol-1,3,5-O-phosphate, which was obtained either by direct phosphorylation of