114342-99-3

Upstream product

• 990-91-0 dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate 
• 16749-97-6 racemic 2,4-di-O-benzyl-myo-inositol 
• 100-39-0 benzyl bromide 
• 98510-20-4 myo-Inositol orthoformate 
• 114828-05-6 4/6-O-allyl-myo-inositol 1,3 5-monoorthoformate 
• 114828-06-7 (+/-) 2,6-di-O-benzyl-4-O-allyl-myo-inositol orthoformate 
• 114419-12-4 (+)-1L-2,6-di-O-benzyl-myo-inositol 
• 108549-23-1 Dibenzyl N,N-diisopropylphosphoramidite 
• 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 

Downstream Products

• 99610-76-1 myo-inositol 1,3,4,5-tetrakisphosphate 

Relevant academic research and scientific papers

Yb(OTf)3-Catalyzed Desymmetrization of myo-Inositol 1,3,5-Orthoformate and Its Application in the Synthesis of Chiral Inositol Phosphates

A variety of inositol phosphates including myo-inositol 1,4,5-trisphosphate, which is a secondary messenger in transmembrane signaling, were selectively synthesized via Yb(OTf)3-catalyzed desymmetrization of myo-inositol 1,3,5-orthoformate using a proline-based chiral anhydride as an acylation precursor. The investigated catalytic system could regioselectively differentiate the enantiotopic hydroxy groups of myo-inositol 1,3,5-orthoformate in the presence of a chiral auxiliary. This key step to generate a suitably protected chiral myo-inositol derivatives is described here as a unified approach to access inositol phosphates.

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).

Synthesis of myo-Inositol 1,3,4,5-Tetraphosphate and myo-Inositol 1,3-Biphosphate

myo-Inositol 1,3,4,5-tetraphosphate, myo-inositol 3,4-biphosphate, and myo-inositol 4-phosphate have been prepared via routes in which a key step is a novel, highly regioselective monooalkylation of myo-inositol orthoformate.