98575-46-3

Upstream product

• 100-39-0 benzyl bromide 
• 98510-20-4 myo-inositol monoorthoformate 
• 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 
• 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 
• 98510-25-9 meso-4,6-di-O-benzyl-D-myo-inositol-1,3,5-O-orthoformate 
• 98510-20-4 myo-Inositol orthoformate 
• 98510-27-1 (1S,5S,7R,8S,9R)-8,9-Bis-benzyloxy-2,4,10-trioxa-tricyclo[3.3.1.1^3,7]decan-6-one 
• 87-89-8 D-myo-inositol 
• 120268-33-9 4/6-O-benzyl-myo-inositol 1,3,5-monoorthoformate 

Downstream Products

• 98510-27-1 (8S,9R)-8,9-Bis-benzyloxy-2,4,10-trioxa-tricyclo[3.3.1.1^3,7]decan-6-one 
• 4922-14-9 Hexaoxadiamantan 
• 114419-12-4 (+)-1L-2,6-di-O-benzyl-myo-inositol 
• 115015-97-9 (-)-1L-2,6-di-O-benzyl-myo-inositol 
• 16749-97-6 racemic 2,4-di-O-benzyl-myo-inositol 
• 135415-09-7 [Fluoro-((1R,2S,3R,4R,5S,6R)-2,3,4,5,6-pentahydroxy-cyclohexyl)-methyl]-phosphonic acid 
• 135346-05-3 [Fluoro-((1S,2R,3S,4R,5R,6S)-2,3,4,5,6-pentahydroxy-cyclohexyl)-methyl]-phosphonic acid 
• 135376-89-5 {[(8S,9R)-8,9-Bis-benzyloxy-2,4,10-trioxa-tricyclo[3.3.1.1^3,7]dec-(6E)-ylidene]-fluoro-methyl}-phosphonic acid diethyl ester 

Relevant academic research and scientific papers

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.

Synthesis of an analogue of D,L-MYO-inositol-1,2-cyclic phosphate: Inhibition of phosphatidylinositol-specific phospholipase C

A fluorophosphonate analogue of myo-inositol-1,2-cyclic phosphate (cIP) has been synthesized: the specific, potent inhibition of a phosphatidyl inositol-specific phospholipase C (PI-PLC) by this compound is compared with inhibition by vanadate ion.

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).