145107-29-5

Basic information

• Product Name: (+)-Conduritol E epoxide
• Synonyms: (+)-Conduritol E epoxide
• CAS NO: 145107-29-5
• Molecular Weight: 162.142
• Mol File: 145107-29-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (+)-Conduritol E epoxide(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Conduritol E epoxide(145107-29-5)
• EPA Substance Registry System: (+)-Conduritol E epoxide(145107-29-5)

Safety Data

• Hazardous Substances Data: 145107-29-5(Hazardous Substances Data)

Upstream product

• 102997-58-0 (1R,2R,3S)-tris(phenylmethoxy)-6S-hydroxy-cyclohex-4-ene 
• 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 
• 110550-28-2 (+)-(1S,2R,3S,4S,5R,6R)-2,3,4,5-tetrakisbenzyloxy-7-oxabicyclo[4.1.0]heptane 
• 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 
• 526-87-4 (+/-)-Conduritol B 
• 526-87-4 conduritol-E 
• 85798-11-4 (4S,5R,6S)-4,5,6-tris-benzyloxycyclohex-2-en-1-one 
• 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 
• 949887-64-3 (1R,2R,3S,6S)-6-(pivaloyloxy)cyclohex-4-ene-1,2,3-triyl triacetate 

Downstream Products

• 110550-28-2 (+)-(1S,2R,3S,4S,5R,6R)-2,3,4,5-tetrakisbenzyloxy-7-oxabicyclo[4.1.0]heptane 
• 852045-24-0 (1S,2R,3S,4R,5R,6S)-N-(2,3,4,5,6-pentakis-benzyloxycyclohexyl)octanamide 

Relevant articles and documents

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.

Improved synthesis of conduritol B epoxide

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