120679-73-4

Upstream product

• 100-39-0 benzyl bromide 
• 38643-30-0 (±)-1,2:5,6-di-O-isopropylidene-myo-inositol 
• 40617-60-5 1,2:5,6-bis-O-(1-methylethylidene)-D-chiro-inositol 
• 87-89-8 D-myo-inositol 
• 115072-66-7 (±)-3,4-di-O-benzoyl-1,2:5,6-di-O-isopropylidene-myo-inositol 

Downstream Products

• 13035-65-9 (±)-1,6-di-O-benzyl-myo-inositol 
• 131147-03-0 (+/-)-3,4-di-O-benzyl-1,2-O-isopropylidene-myo-inositol 
• 110550-28-2 (+)-(1S,2R,3S,4S,5R,6R)-2,3,4,5-tetrakisbenzyloxy-7-oxabicyclo[4.1.0]heptane 
• 110550-24-8 1D-2,3,4,5-tetra-O-benzyl-chiro-inositol 
• 6090-95-5 (+)-(1R,2R,3S,4S,5R,6S)-2,3,4,5-tetraol-7-oxabicyclo[4.1.0]heptane 
• 120710-66-9 (1S,2S,3S,4R,5S,6R)-5,6-di(benzyloxy)cyclohexane-1,2,3,4-tetrol 
• 131147-10-9 4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (3aS,4S,5R,6S,7S,7aS)-5,6,7-tris-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl ester 
• 131147-10-9 4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (3aR,4R,5S,6R,7R,7aR)-5,6,7-tris-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl ester 
• 131233-67-5 1,4,5,6-tetra-O-benzyl-2,3-isopropylidene-sn-myo-inositol 
• 131233-64-2 3,4,5,6-tetra-O-benzyl-1,2-isopropylidene-sn-myo-inositol 
• 261722-84-3 1,3,4,5-Tetra-O-benzyl-D-myo-inositol 
• 131147-14-3 1D-1,3,5,6-tetra-O-benzyl-myo-inositol 
• 131233-74-4 2-O,3-O,4-O,5-O-tetrabenzyl-L-myo-inositol 
• 131233-72-2 1,6-di-O-allyl-3,4,5-tri-O-benzyl-L-myo-inositol 

Relevant academic research and scientific papers

New syntheses of 1D- and 1L-1,2-anhydro-myo-inositol and assessment of their glycosidase inhibitory activities

The 1D and 1L enantiomers of 1,2-anhydro-myo-inositol (conduritol B epoxide) were synthesised from 1d-pinitol and 1l-quebrachitol, respectively, and their activities were compared in selected glycosidase inhibition assays. The 1d enantiomer was found to be the active isomer, functioning as an irreversible inhibitor of sweet almond β-D-glucosidase. Neither isomer was active against the α-D-glucosidase from Bacillus stearothermophilus or the β-D-galactosidase from Aspergillus oryzae. (C) 2000 Elsevier Science Ltd.

Practical synthesis of all inositol stereoisomers from myo-inositol

Synthesis of six inositol stereoisomers was successfully carried out via conduritol intermediates prepared from myo-inositol. Dihydroxylation and epoxidation followed by ring opening of the conduritol B, C and F derivatives gave epi-, allo-, muco-, neo-, DL-chiro- and scyllo-inositol. The cis- inositol derivative, which may not be prepared by this approach, was synthesized in 5 steps via 2-O-benzoyl-myo-inositol orthoformate as the key intermediate.

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.

The synthesis and resolution of (+/-)-1,5,6-tri-O-benzyl-myo-inositol

Racemic 1,5,6-O-benzyl-myo-inositol was prepared by five routes and converted into 1,5,6-tri-O-benzyl-2,3-O-isopropylidene-myo-inositol, the camphanates of which were readily separated by chromatography.The absolute configurations of the chiral derivative