110550-28-2

Upstream product

• 110550-24-8 1D-2,3,4,5-tetra-O-benzyl-chiro-inositol 
• 120679-73-4 1D-1,2:5,6-di-O-isopropylidene-3,4-di-O-benzyl-chiro-inositol 
• 120710-66-9 (1S,2S,3S,4R,5S,6R)-5,6-di(benzyloxy)cyclohexane-1,2,3,4-tetrol 
• 40617-60-5 1,2:5,6-bis-O-(1-methylethylidene)-D-chiro-inositol 
• 100-39-0 benzyl bromide 
• 949887-64-3 (1R,2R,3S,6S)-6-(pivaloyloxy)cyclohex-4-ene-1,2,3-triyl triacetate 
• 4381-96-8 (+/-)-(1,3/2,4)-1,2,3,4-tetra-O-acetyl-5-cyclohexene-1,2,3,4-tetrol 
• 138258-55-6 (1S,2R,3R,4S)-1,2,3,4,tetrahydroxy-5-cyclohexene 
• 6090-95-5 (+)-(1R,2R,3S,4S,5R,6S)-2,3,4,5-tetraol-7-oxabicyclo[4.1.0]heptane 
• 133218-74-3 4,5,6-tri-O-benzyl-1,2-anhydro-myo-inositol 

Downstream Products

• 950170-55-5 (+)-(1R,2S,3S,4R,5S,6R)-(2-azido-3,4,5,6-tetrakisbenzyloxy)cyclohexyl methanesulfonate 
• 949887-65-4 (+)-(1S,2R,3S,4R,5R,6S)-2-azido-3,4,5,6-tetrakisbenzyloxycyclohexanol 
• 949887-66-5 (-)-(1S,2R,3S,4R,5R,6S)-2-amino-3,4,5,6-tetrakisbenzyloxycyclohexanol 
• 864948-63-0 (+)-(1R,2R,3S,4R,5R,6S)-2-azido-3,4,5,6-tetrakisbenzyloxycyclohexanol 
• 6090-95-5 (+)-(1R,2R,3S,4S,5R,6S)-2,3,4,5-tetraol-7-oxabicyclo[4.1.0]heptane 

Relevant academic research and scientific papers

An unexpected chelation-controlled Yb(OTf)3-catalyzed aminolysis and azidolysis of cyclitol epoxides

A chelation-controlled aminolysis and azidolysis of cyclitol epoxides with Yb(OTf)3 has been disclosed. The presence of a free OH group able to direct the coordination with the lanthanide seems essential for an efficient regiocontrol of the pro

Practical synthesis of (-)-1-amino-1-deoxy-myo-inositol from achiral precursors

A new synthesis of enantiomerically pure 1-amino-1-deoxy-myo-inositol is reported. The route described employs p-benzoquinone, an achiral compound, as the starting material to give conduritol B tetraacetate in three steps. Kinetic resolution of this compound using a palladium catalyst with a chiral ligand allows access to a conduritol B tetraester in high enantiomeric excess. This compound is transformed into tetrabenzyl conduritol B epoxide, which is regioselectively opened with azide to give the key azidocyclitol. Final transformation into (-)-1-amino-1-deoxy-myo-inositol hydrochloride is achieved in four synthetic steps. This sequence allows the synthesis of this compound in high enantiomeric purity in a semi-preparative scale.

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.