6090-95-5

Basic information

• Product Name: CONDURITOL B EPOXIDE
• Synonyms: conduritolepoxide;CBE;(+/-) CONDURITOL B EPOXIDE;CONDURITOL B EPOXIDE;DL-1,2-ANHYDRO-MYO-INOSITOL;myo-Inositol, 1,2-anhydro- (9CI);1,2-Anhydro-myo-inositol;(1R,2R,3S,4S,5R,6S)-7-oxabicyclo[4.1.0]heptane-2,3,4,5-tetrol
• CAS NO: 6090-95-5
• Molecular Formula: C₆H₁₀O₅
• Molecular Weight: 162.14
• Product Categories: EPOXYDE;All Inhibitors;Glycosidase Inhibitors;Inhibitors;api
• Mol File: 6090-95-5.mol

Chemical Properties

• Melting Point: 157-159
• Boiling Point: 360.478 °C at 760 mmHg
• Flash Point: 171.811 °C
• Appearance: white crystalline solid
• Density: 1.925±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.732
• Storage Temp.: 2-8°C
• Solubility: Soluble in Water (up to 25 mg/ml) or in DMSO
• PKA: 13.08±0.70(Predicted)
• Stability: Moisture Sensitive
• CAS DataBase Reference: CONDURITOL B EPOXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: CONDURITOL B EPOXIDE(6090-95-5)
• EPA Substance Registry System: CONDURITOL B EPOXIDE(6090-95-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 6090-95-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
CONDURITOL B EPOXIDE is used as an inhibitor of glucosidases for targeting and inhibiting the activity of various b-glucosidases from different sources such as Aspergillus species, yeast, snail, sweet almonds, and mammals. It also covalently inhibits a-glucosidase from yeast and the sucrase-isomaltase complex from rabbit small intestine.
Used in Research and Development:
CONDURITOL B EPOXIDE is used as a research tool for the generation of the "Gaucher mouse" and the in vitro model of the Gaucher cell, which aids in understanding the mechanisms and potential treatments for Gaucher disease, a genetic disorder caused by a deficiency of glucocerebrosidase enzyme activity.

Biochem/physiol Actions

Conduritol B epoxide?(CBE)?is capable of inactivating sucrase-isomaltase irreversibly. It can be used to produce cell and animal models to study on Gaucher disease (GD) and Parkinson′s disease (PD).

References

1) Datta and Radin (1988), Normalization of liver glucosylceramide levels in the “Gaucher” mouse by phosphatidylserine injection;? Biochem. Biophys. Res. Commun., 152 155 2) Radin and Vunnam (1981), Inhibitors of cerebroside metabolism;? Methods Enzymol., 72 673 3) Stephens et al. (1981), Distribution of conduritol B epoxide in the animal model for gaucher’s disease (Gaucher mouse); Biochim. Biophys. Acta, 672 29 4) Newburg et al. (1986), beta-Glucosidase inhibition in murine peritoneal macrophages by conduritol-B-epoxide: an in vitro model of the Gaucher cell;? Biochim. Biophys. Acta, 877 121

InChI:InChI=1/C6H10O5/c7-1-2(8)4(10)6-5(11-6)3(1)9/h1-10H/t1-,2-,3+,4+,5?,6?/m1/s1

Upstream product

• 138258-55-6 (1S,2R,3R,4S)-1,2,3,4,tetrahydroxy-5-cyclohexene 
• 40617-60-5 1,2:5,6-bis-O-(1-methylethylidene)-D-chiro-inositol 
• 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 
• 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 
• 4381-96-8 (+/-)-(1,3/2,4)-1,2,3,4-tetra-O-acetyl-5-cyclohexene-1,2,3,4-tetrol 
• 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 

Downstream Products

• 488-54-0 neo-inositol 
• 20097-40-9 hexa-O-acetyl-neo-inositol 
• 29267-04-7 hexa-O-acetyl allo-inositol 
• 110550-28-2 (+)-(1S,2R,3S,4S,5R,6R)-2,3,4,5-tetrakisbenzyloxy-7-oxabicyclo[4.1.0]heptane 
• 864948-63-0 (+)-(1R,2R,3S,4R,5R,6S)-2-azido-3,4,5,6-tetrakisbenzyloxycyclohexanol 
• 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 
• 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.

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.