25348-64-5

Basic information

• Product Name: CONDURITOL B
• Synonyms: (+/-) CONDURITOL B;CONDURITOL B;(1S)-5-Cyclohexene-1α,2β,3α,4β-tetrol;[1S,(+)]-5-Cyclohexene-1α,2β,3α,4β-tetrol;(1R,2S,3S,4R)-Cyclohex-5-ene-1,2,3,4-tetrol;(1R,2S,3S,4R)-rel-5-Cyclohexene-1,2,3,4-tetrol
• CAS NO: 25348-64-5
• Molecular Formula: C₆H₁₀O₄
• Molecular Weight: 146.14
• Product Categories: All Inhibitors;Glycosidase Inhibitors;Inhibitors
• Mol File: 25348-64-5.mol
• Article Data: 23

Chemical Properties

• Melting Point: 201-203
• Boiling Point: 281.9 °C at 760 mmHg
• Flash Point: 141.3 °C
• Appearance: /
• Density: 1.666 g/cm³
• Vapor Pressure: 0.000409mmHg at 25°C
• Refractive Index: 1.693
• Storage Temp.: -20°C Freezer
• Solubility: DMSO, Water
• CAS DataBase Reference: CONDURITOL B(CAS DataBase Reference)
• NIST Chemistry Reference: CONDURITOL B(25348-64-5)
• EPA Substance Registry System: CONDURITOL B(25348-64-5)

Safety Data

• Hazardous Substances Data: 25348-64-5(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Conduritol b acts on b-glucosidases from widely differing sources to show a loss of enzymic activity: from various Aspergillus species, yeast, snail, sweet almonds, and mammals. The other enzymes that have been found to be covalently inhibited are a- glucosidase from yeast and the sucrase-isomaltase complex from rabbit small intestine.

InChI:InChI=1/C6H10O4/c7-3-1-2-4(8)6(10)5(3)9/h1-10H/t3-,4-,5+,6+/m0/s1

Upstream product

• 371155-83-8 (3aS,4S,7R,7aS)-3a,4,7,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-4,7-diol dibenzoate 
• 4381-96-8 (+/-)-1,2,3,4-tetra-O-acetylconduritol E 
• 4381-96-8 (+/-)-tetra-O-acetylconduritol F 
• 38643-30-0 (±)-1,2:5,6-di-O-isopropylidene-myo-inositol 
• 13035-65-9 (±)-1,6-di-O-benzyl-myo-inositol 
• 120679-73-4 (+/-)-3,4-di-O-benzyl-1,2:5,6-di-O-isopropylidene-myo-inositol 
• 115072-66-7 (±)-3,4-di-O-benzoyl-1,2:5,6-di-O-isopropylidene-myo-inositol 
• 4381-96-8 (+/-)-(1,3/2,4)-1,2,3,4-tetra-O-acetyl-5-cyclohexene-1,2,3,4-tetrol 
• 17793-95-2 cis-1,2-dihydrocatechol 
• 4381-96-8 (+/-)-tetraacetylconduritol C 
• 99756-37-3 (±)-3,6-di-O-benzoyl-1,2:4,5-di-O-isopropylidene-myo-inositol 
• 88708-22-9 (+)-(1R,4R)-7-oxabicyclo<2.2.1>-hept-5-en-2-one 
• 371155-82-7 (3aS,4R,7R,7aS)-3a,4,7,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-4,7-diol 4-monobenzoate 
• 371155-64-5 (3aS,4R,7R,7aS)-3a,4,7,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-4,7-diol 

Downstream Products

• 18779-57-2 1,2,3,4,5,6-hexa-O-acetyl-muco-inositol 
• 61825-76-1 (+/-)-1-bromo-1-deoxyconduritol F 
• 61825-76-1 (+/-)-1-bromo-1-deoxyconduritol B 
• 2671-07-0 Penta-O-acetyl-5-brom-5-desoxy-rac-inosit 
• 347377-81-5 (+)-(1S,2R,3R,4S)-1,4-Dibenzoyloxy-5-cyclohexene-2,3-diol 
• 253584-54-2 (+)-(1S,2R,3R,4S)-1,4-Dibenzoyloxy-2,3-di[(2,2,2-trichloroethoxy)carbonyl]oxy-5-cyclohexene 
• 347377-79-1 C₂₈H₂₃NO₆ 

Relevant articles and documents

Concise synthesis of (+)-conduritol F and inositol analogues from naturally available (+)-proto-quercitol and their glucosidase inhibitory activity

An effective synthesis of (+)-conduritol F, (+)-chiro- and (+)-epi-inositols from naturally available (+)- proto-quercitol is described. This synthetic method provides a concise synthesis of cyclitols in enantiomerically pure form. Of the synthesized cyclitols, (+)-conduritol F potently inhibits type I α-glucosidase with an IC50 value of 86.1 lM, which is five times greater than the standard antidiabetic drug, acarbose.

Directed dihydroxylation of cyclic allylic alcohols and trichloroacetamides using OsO4/TMEDA

The oxidation of a range of cyclic allylic alcohols and amides with OsO4/TMEDA is presented. Under these conditions, hydrogen bonding control leads to the (contrasteric) formation of the syn isomer in almost every example that was examined. Evidence for the bidentate binding of TMEDA to OsO4 is presented and a plausible mechanism described.

Facile syntheses of all possible diastereomers of conduritol and various derivatives of inositol stereoisomers in high enantiopurity from myo-inositol

Phosphoinositide-based signaling processes are crucially important in intracellular signal transduction events. Inositol phosphate analogues have been useful in probing the structure-activity relationships between inositol phosphates and biomacromolecules, and in studying biological functions of newly found inositol phosphates. Thus, a systematic and ready access to inositol stereoisomers is highly desirable. And practical and convenient syntheses of conduritols and related compounds are also important because of their biological activities and their synthetic utilities in the preparation of other bioactive molecules. We herein report the first syntheses of all possible diastereomers of conduritol and various derivatives of eight inositol stereoisomers in high enantiopurity from myo-inositol, which involve efficient enzymatic resolution of the intermediates conduritol B and C derivatives, followed by oxidation-reduction or the Mitsunobu reaction, and cis-dihydroxylation in stereo- and regioselective manners.