33800-41-8

Upstream product

• 526-87-4 conduritol-E 
• 526-87-4 (+/-)-Conduritol B 
• 110550-28-2 (+)-(1S,2R,3S,4S,5R,6R)-2,3,4,5-tetrakisbenzyloxy-7-oxabicyclo[4.1.0]heptane 
• 138258-55-6 (1S,2R,3R,4S)-1,2,3,4,tetrahydroxy-5-cyclohexene 
• 102997-58-0 (1R,2R,3S)-tris(phenylmethoxy)-6S-hydroxy-cyclohex-4-ene 
• 85798-11-4 (4S,5R,6S)-4,5,6-tris-benzyloxycyclohex-2-en-1-one 
• 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 
• 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 
• 133218-74-3 4,5,6-tri-O-benzyl-1,2-anhydro-myo-inositol 
• 39110-61-7 3,4,5,6-tetra-O-acetyl-1,2-O-cyclohexylidene-myo-inositol 
• 25348-62-3 Acetic acid (3aR,4R,5S,6S,7R,7aS)-5,6,7-triacetoxy-2-thioxo-hexahydro-benzo[1,3]dioxol-4-yl ester 
• 13462-79-8 1⁽³⁾,4⁽⁶⁾,5,6⁽⁴⁾-tetra-O-acetyl-sn-myo-inositol 

Downstream Products

• 488-54-0 neo-inositol 
• 20097-40-9 hexa-O-acetyl-neo-inositol 
• 29267-04-7 hexa-O-acetyl allo-inositol 
• 868550-22-5 (1S,2S,3R,4R,5S,6R)-1-azido-2,3,4,5,6-pentakis-benzyloxycyclohexane 

Relevant academic research and scientific papers

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.

Regio- and stereoselective synthesis of aminoinositols and 1,2-diaminoinositols from conduritol B epoxide

A systematic approach to the regio- and stereoselective synthesis of aminoinositols and 1,2-diaminoinositols arising from tetra-O-benzylconduritol B epoxide (9) and its aziridine analogue 22, respectively, is described. In all cases, the synthetic methodologies rely on the regio- and stereocontrolled azidolysis of the starting precursors to give the corresponding trans regioadducts. Subsequent functional group manipulation under strict configurational control affords the isomeric cis adducts. Chemoselective functionalization of the diamine moiety in 1,2-diaminoinositol derivatives can be achieved by the proper design of the reaction sequence and choice of reagents. The described protocols allow efficient access to each of the eight possible configurations of the 1,2-diamino and 1,2-amino alcohol moieties from chemical modifications of the epoxide moiety on the common precursor 9.

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.