99610-76-1

Upstream product

• 126960-08-5 C₅₂H₅₂O₁₈P₄ 
• 114342-99-3 (+/-) 2,6-di-O-benzyl-myo-inositol 1,3,4,5-tetrakis(dibenzylphosphate) 
• 98510-20-4 myo-Inositol orthoformate 
• 114828-05-6 4/6-O-allyl-myo-inositol 1,3 5-monoorthoformate 
• 115015-98-0 octabenzyl 1D-2,6-di-O-benzyl-myo-inositol 1,3,4,5-tetrakisphosphate 
• 140696-30-6 (1R,2S,3R,6R)-2-bromo-7-oxabicyclo[4.1.0]hept-4-en-3-ol 
• 864950-98-1 (1R,2S,3R,6S)-6-benzyloxy-2-bromocyclohex-4-ene-1,3-diol 
• 864951-01-9 (1S,2R,3R,4S)-1-O-benzylconduritol B 
• 864951-09-7 (1S,2R,3S,6R)-3-Benzyloxy-7-oxa-bicyclo[4.1.0]hept-4-en-2-ol 
• 135195-52-7 C₅₀H₆₈O₁₈P₄Si₂ 
• 114828-06-7 (+/-) 2,6-di-O-benzyl-4-O-allyl-myo-inositol orthoformate 
• 16749-97-6 racemic 2,4-di-O-benzyl-myo-inositol 
• 115133-07-8 (1R,5S,6S,7R,8S,9R)-6,8-Bis-benzyloxy-9-benzyloxymethoxy-2,4,10-trioxa-tricyclo[3.3.1.1^3,7]decane 

Relevant academic research and scientific papers

Flexible stereo- and regioselective synthesis of myo-inositol phosphates (Part 2): Via nonsymmetrical conduritol B derivatives

A practical route is described for the preparation of myo-inositol phosphates. Optically pure compounds can be prepared, in both forms, from p-benzoquinone by enzymatic resolution of a diacetoxyconduritol key intermediate. Monosubstituted inositol derivat

Divergent syntheses of all possible optically active regioisomers of myo-inositol tris- and tetrakisphosphates

Since the discovery of D-myo-inositol 1,4,5-trisphosphate, which plays a pivotal role as a second messenger in transmembrane signaling, the scope of the phosphoinositide-based signaling processes has been continually expanding. However, the clear understanding of the molecular signal transduction mechanisms including the functions of newly found IPn is still lacking. As a continuing effort to our previously reported syntheses of all possible 39 optically inactive regioisomers of myoinositol phosphates (IPn; n = 1-6), we synthesized all possible optically active regioisomers of myo-IP3 and myo-IP4 using chiral IBz3s and IBz2s, respectively. A series of procedures involving CRL-catalyzed enzymatic resolution of racemic 1,2:5,6-di-O-isopropylidene-myo-inositol and base-catalyzed benzoyl migration in tri- and dibenzoyl-isopropylidene-myo-inositol afforded eight enantiomeric pairs of IBz3 and six enantiomeric pairs of IBz2, respectively. Phosphorylation of these intermediates by the phosphitylation and oxidation procedure gave the target products.

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.

AN EFFICIENT ROUTE TO D-MYO-INOSITOL 1,3,4-TRIPHOSPHATE AND D-MYO-INOSITOL 1,3,4,5-TETRAKISPHOSPHATE

Multigram quantities of the title compounds in their enantiomerically-pure forms have been prepared by employing a chiral precursor which can be obtained via a facile enzymatic process.

A Short Step Synthesis of Optically Active myo-Inositol 1,3,4,5-Tetrakis(phosphate) and myo-Inositol 1,4,5-Tris(phosphate) from 1,3,5-Tri-O-benzoyl-myo-inositol

A short and practical synthesis of myo-inositol 1,3,4,5-tetrakis(phosphate) and myo-inositol 1,4,5-tris(phosphate) has been achieved by direct benzoylation of myo-inositol, enantioselective tartaroylation and removal of acyl protecting groups with Grignar

The Total Synthesis of myo-Inositol Phosphates via myo-Inositol Orthoformate

Novel selective alkylations of myo-inositol orthoformate (4) have been used to prepare a series of protected myo-inositol derivatives, (5a-e), (7), (10), (12), and (16).These intermediates have been used in efficient total syntheses of myo-inositol 2-phosphate, (9); myo-inositol 4-phosphate, (6); myo-inositol 1,3-bisphosphate, (18); and myo-inositol 1,3,4,5-tetrakisphosphate (14).This report represents the first total synthesis of the important natural metabolites (14) and (18) and significantly improved methods of preparation of (6) and (9).

TOTAL SYNTHESIS OF OPTICALLY ACTIVE MYO-INOSITOL 1,4,5-TRISPHOSPHATE AND MYO-INOSITOL 1,3,4,5-TETRAKISPHOSPHATE

A convenient approach to the preparation of the title compounds illustrating selective protection, optical resolution and phosphorylation is presented.