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

Description

CONDURITOL B is a white solid that is known for its ability to inhibit 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.

Uses

Used in Pharmaceutical Industry:
CONDURITOL B is used as an inhibitor for b-glucosidases and a-glucosidase, which are essential enzymes in the metabolism of carbohydrates. Its inhibition properties make it a valuable compound in the development of drugs targeting carbohydrate metabolism-related diseases.
Used in Research and Development:
CONDURITOL B is used as a research tool to study the function and inhibition of b-glucosidases and other related enzymes. This helps in understanding the underlying mechanisms of carbohydrate metabolism and the development of potential therapeutic strategies.
Used in Enzyme Inhibition Studies:
CONDURITOL B is used as a specific inhibitor for b-glucosidases and a-glucosidase in enzyme inhibition studies. This allows researchers to investigate the role of these enzymes in various biological processes and their potential as therapeutic targets.
Used in Biochemical Analysis:
CONDURITOL B is used in biochemical analysis to determine the presence and activity of b-glucosidases and a-glucosidase in different samples, such as tissues, cells, or biological fluids. This information can be useful in diagnosing and monitoring carbohydrate metabolism-related disorders.

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

• 538334-59-7 (1S,2S,5R,6R)-5,6-di(benzyloxy)cyclohex-3-ene-1,2-diol 
• 129745-62-6 (-)-(4R,5S,6R)-4,5,6-tris(<(tert-butyl)dimethylsilyl>oxy)cyclohex-2-en-1-one 
• 129745-63-7 (-)-1D-2,3,4-tris-O-<(tert-butyl)dimethylsilyl>cyclohex-2-ene-1,2,4/3-tetrol 
• 129829-55-6 (-)-(1R,4R,5R,6R)-5-exo,6-endo-bis(<(tert-butyl)dimethylsilyl>oxy)-7-oxabicyclo<2.2.1>heptan-2-one 
• 129829-54-5 (-)-(1R,4R,5R,6S)-6-endo-(benzyloxy)-5-exo-hydroxy-7-oxabicyclo<2.2.1>heptan-2-one 
• 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 
• 538334-67-7 (3S,4R,5S,6R)-5,6-dibenzyloxy-3-(dimethylphenylsilanyl)octa-1,7-dien-4-ol 
• 538334-70-2 (1R,2S,5R,6R)-5,6-dibenzyloxy-2-(dimethylphenylsilanyl)cyclohex-3-enol 
• 535994-37-7 (2S,3R)-2,3-dibenzyloxy-4-penten-1-al 
• 17793-95-2 cis-1,2-dihydrocatechol 
• 371155-83-8 (3aS,4S,7R,7aS)-3a,4,7,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-4,7-diol dibenzoate 
• 129829-60-3 (+)-Tetra-O-acetylconduritol F 

Downstream Products

• 2975-92-0 (+/-)-cyclohexane-1r,2c,3t,4t-tetraol 
• 6090-95-5 (+/-)-1,2-anhydro-allo-inositol 
• 2975-92-0 (+/-)-1D-cyclohexane-1,2,4/3-tetrol 
• 6090-95-5 conduritol β-epoxide 
• 2975-92-0 d,l-(1,2,3/4)-cyclohexanetetrol 
• 18779-57-2 1,2,3,4,5,6-hexa-O-acetyl-muco-inositol 
• 2975-92-0 (+/-)-1L-cyclohexane-1,3/2,4-tetrol 
• 4381-96-8 (+/-)-1,2,3,4-tetra-O-acetylconduritol E 
• 4381-96-8 (+/-)-tetraacetylconduritol C 
• 61825-76-1 (+/-)-1-bromo-1-deoxyconduritol F 
• 61825-76-1 (+/-)-1-bromo-1-deoxyconduritol B 
• 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 

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.

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.

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.