65533-41-7

Upstream product

• 100-39-0 benzyl bromide 
• 65556-81-2 1L-1,2:5,6-di-O-isopropylidene-chiro-inositol 
• 90694-04-5 1L-1,2:3,4:5,6-tri-O-isopropylidene-chiro-inositol 
• 116-11-0 2-Methoxypropene 
• 23486-90-0 (+/-) 1-O-benzyl-myo-inositol 
• 77-76-9 2,2-dimethoxy-propane 
• 38643-30-0 (±)-1,2:5,6-di-O-isopropylidene-myo-inositol 
• 87-89-8 D-myo-inositol 
• 6404-82-6 (+/-)-1,2-O-isopropylidene-myo-inositol 
• 115072-66-7 (±)-3,4-di-O-benzoyl-1,2:5,6-di-O-isopropylidene-myo-inositol 

Downstream Products

• 90626-62-3 1L-3-O-Acetyl-4-O-benzyl-1,2:5,6-di-O-isopropyliden-chiro-inosit 
• 52079-86-4 (1R)-(+)-(1,2,3/4,5)-2,3,4,5-tetrahydroxycyclohexane-1-methanol penta-acetate 
• 52079-85-3 (1R)-(+)-(1,2,3/4,5)-2,3,4,5-tetrahydroxycyclohexane-1-methanol 
• 90626-78-1 1L-(1,2,3,5/4)-5-(2-Acetoxymethyl-1,3-dithian-2-yl)-1-O-acetyl-4-O-benzyl-2,3-O-isopropyliden-1,2,3,4-cyclohexantetrol 
• 90626-79-2 2L-(2,3,5/4)-4-O-Benzyl-5-(2-ethoxycarbonyl-1,3-dithian-2-yl)-2,3-O-isopropyliden-2,3,4-trihydroxycyclohexanon 
• 90626-66-7 1L-4-O-Benzyl-3-desoxy-1,2:5,6-di-O-isopropyliden-3-C-<(2-methoxyethoxy)methoxymethyl>-allo-inosit 
• 90626-84-9 Acetic acid (3aR,4R,6S,7R,7aS)-6-(2-acetoxy-acetyl)-7-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl ester 
• 90626-82-7 1L-(1,2,3,5/4)-5-Acetoxymethyl-1-O-acetyl-4-O-benzyl-2,3-O-isopropyliden-1,2,3,4-cyclohexantetrol 
• 90652-13-4 1L-3-C-Acetoxymethyl-4-O-benzyl-3-desoxy-1,2:5,6-di-O-isopropyliden-allo-inosit 
• 90626-70-3 2D-(2,3,6/4,5)-6-O-Benzyl-2,3:4,5-di-O-isopropyliden-1-methoxymethylen-2,3,4,5,6-cyclohexanpentol 
• 90626-83-8 (3aR,4R,6S,7R,7aS)-7-Benzyloxy-6-(2-hydroxymethyl-[1,3]dithian-2-yl)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-ol 
• 90626-88-3 Acetic acid (1R,2R,3R,4S,5R)-5-acetoxy-2-benzyloxy-3,4-dihydroxy-cyclohexylmethyl ester 
• 90626-63-4 2D-(2,3,6/4,5)-6-O-Benzyl-2,3:4,5-di-O-isopropyliden-1-methylen-2,3,4,5,6-cyclohexan-pentol 
• 90626-65-6 1L-4-O-Benzyl-3-desoxy-3-C-hydroxymethyl-1,2:5,6-di-O-isopropyliden-allo-inosit 

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.

Regioselective functionalizations and conformational studies of di-O-isopropylidene-myo-inositol derivatives

(+/-)-1,2:4,5-Di-O-isopropylidene-myo-inositol (5) and (+/-)-1,2:5,6-di-O-isopropylidene-myo-inositol (6) could be regioselectively functionalized in reactions including alkylation, acylation, and silylation at HO-3 in preference to HO-6 and HO-4, respectively, under specific conditions.The presence of intramolecular hydrogen bonding was evident in IR and 1H NMR spectra, and the HO-3 group was identified as the hydrogen-bonding donor in 5 and 6.In their crystalline states, diol 5 prefers a chair conformation and diol 6 a twist boat (skew) conformation.Both compounds appear to have substantial populations of chair conformations in the gas and solution phases, on the basis of the MM-2 energy minimizations and comparisons of vicinal coupling constants observed in the 1H NMR spectra (in CDCl3 and Me2SO-d6) and calculated from the crystal and MM-2 conformations.It is suggested as an explanation for the observed selectivities that the kinetic acidity of the HO-3 group may be enhanced through its intramolecular hydrogen bonding with the cis-vicinal oxygen, or the nucleophilicity of the 3-alkoxide may be enhanced due to its interaction with the cis-vicinal oxygen in a manner similar to the through-space α-effect.

Improved preparation of acetals of myo-inositol and its (+/-)-1-benzyl ether: conformational analysis of di-O-isopropylidene-myo-inositol derivatives

The acid-catalysed reactions of myo-inositol with 3-5 equiv. of 2-methoxypropene or 2,2-dimethoxypropane in methyl sulfoxide or N,N-dimethylformamide gave mixtures of the 1,2:4,5-, 1,2:5,6-, and 1,2:3,4-di-O-isopropylidene derivatives with little or none

Cyclitol Reactions, X. - Synthesis of Enantiomerically Pure Pseudo-α-D-galactopyranose and Pseudo-β-D-mannopyranose

The L-chiro-inositol 2, prepared from quebrachitol, is transferred, via 5, into the inosose 7.Wittig reaction of 7 and subsequent hydroboration followed by oxidation leads to the hydroxymethyl branched-chain derivative 8.From this, via 11, the S-methyl di