139640-12-3

Upstream product

• 139686-87-6 (3aS,4S,5S,5aR,8aS,8bS)-5-Benzyloxy-2,2,7,7-tetramethyl-hexahydro-benzo[1,2-d;3,4-d']bis[1,3]dioxol-4-ol 
• 139640-11-2 Carbonic acid (3aR,4S,5R,5aR,8aS,8bR)-5-benzyloxy-2,2,7,7-tetramethyl-hexahydro-benzo[1,2-d;3,4-d']bis[1,3]dioxol-4-yl ester (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 139640-09-8 1-O-menthoxycarbonyl-2,3:4,5-di-O-isopropylidene-myo-inositol 
• 207131-20-2 Carbonic acid (3aR,4S,5R,5aR,8aS,8bR)-5-benzyloxy-2,2,7,7-tetramethyl-hexahydro-benzo[1,2-d;3,4-d']bis[1,3]dioxol-4-yl ester (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester 

Downstream Products

• 207128-85-6 4-O-benzyl-1,2-O-isopropylidene-myoinositol 3,5,6-tris(dibenzyl phosphate) 
• 2068-89-5 D-myo-inositol 1,4,5-triphosphate 

Relevant academic research and scientific papers

A convenient synthesis of D-myo-inositol 1,4,5-trisphosphate (Ins(1,4,5)P3) and L-myo-inositol 1,4,5-trisphosphate (Ins(3,5,6)P3)

An efficient synthesis of an optically active inositol derivative that is a precursor to D-myo-inositol 1,4,5-trisphosphate (Ins(1,4,5)P3, (-)) is described. Crystallization of the diastereomers of (±) -1-O-[(+)- menthoxycarbonyl]-6-O-benzyl-2,3:4,5-di-O-isopropylidene-myo-inositol diastereomers from methanol gives only one diastereomer. Alkaline hydrolysis gives the useful inositol derivative (-)-6-O-benzyl-2,3:4,5-di-O- isopropylidene-myo-inositol. Likewise, crystallization of the diastereomers of (±)-3-O-[(-)-menthoxycarbonyl]-4-O-benzyl-1,2:5,6-di-O-isopropylidene- myo-inositol from methanol gave a pure compound which could be hydrolyzed to give (+)-4-O-benzyl-1,2:5,6-di-O-isopropylidene-myo-inositol, a precursor to D-myo-inositol 3,5,6-trisphosphate (Ins(3,5,6)P3, (+)). The ease with which these enantiomerically pure inositol derivatives were isolated may facilitate the synthesis of more complex inositol phosphate derivatives such as D-myo- inositol 1,3,4,5-tetrakisphosphate.

The regioselective synthesis of enantiomerically pure myo-inositol derivatives. Efficient synthesis of myo-inositol 1,4,5-trisphosphate

Regioselective 1-O-acylation of myo-inositol and simultaneous optical resolution has been achieved by perborylation, transmetallation using di-n-butyltin-bis-acetylacetonate and then acylation with (-)-menthyl chloroformate. Diastereomerically pure 1-O-(-