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

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

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

• 371155-83-8 (3aS,4S,7R,7aS)-3a,4,7,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-4,7-diol dibenzoate 
• 538334-59-7 (1S,2S,5R,6R)-5,6-di(benzyloxy)cyclohex-3-ene-1,2-diol 
• 538334-70-2 (1R,2S,5R,6R)-5,6-dibenzyloxy-2-(dimethylphenylsilanyl)cyclohex-3-enol 
• 538334-67-7 (3S,4R,5S,6R)-5,6-dibenzyloxy-3-(dimethylphenylsilanyl)octa-1,7-dien-4-ol 
• 371155-82-7 (3aS,4R,7R,7aS)-3a,4,7,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-4,7-diol 4-monobenzoate 
• 88708-22-9 (+)-(1R,4R)-7-oxabicyclo<2.2.1>-hept-5-en-2-one 
• 94482-74-3 (+)-(1R,2R,4R)-2-endo-cyano-7-oxabicyclo<2.2.1>hept-5-ene-2-exo-yl acetate 
• 126372-05-2 (+)-(1R,4R)-5,5-bis(benzyloxy)-7-oxabicyclo<2.2.1>hept-2-ene 
• 129829-54-5 (-)-(1R,4R,5R,6S)-6-endo-(benzyloxy)-5-exo-hydroxy-7-oxabicyclo<2.2.1>heptan-2-one 
• 129829-55-6 (-)-(1R,4R,5R,6R)-5-exo,6-endo-bis(<(tert-butyl)dimethylsilyl>oxy)-7-oxabicyclo<2.2.1>heptan-2-one 
• 129745-63-7 (-)-1D-2,3,4-tris-O-<(tert-butyl)dimethylsilyl>cyclohex-2-ene-1,2,4/3-tetrol 
• 129745-62-6 (-)-(4R,5S,6R)-4,5,6-tris(<(tert-butyl)dimethylsilyl>oxy)cyclohex-2-en-1-one 
• 1157852-09-9 1,2:3,4-di-O-isopropylidene-5R-(+)-proto-quercitol 
• 1360452-45-4 C₁₂H₁₈O₄ 

Downstream Products

• 2975-92-0 (+/-)-cyclohexane-1r,2c,3t,4t-tetraol 
• 6090-95-5 (+/-)-1,2-anhydro-allo-inositol 
• 4381-96-8 (+/-)-1,2,3,4-tetra-O-acetylconduritol E 
• 2671-07-0 Penta-O-acetyl-5-brom-5-desoxy-rac-inosit 
• 2975-92-0 (+/-)-1D-cyclohexane-1,2,4/3-tetrol 
• 18779-57-2 1,2,3,4,5,6-hexa-O-acetyl-muco-inositol 
• 6090-95-5 conduritol β-epoxide 
• 2975-92-0 (+/-)-1L-cyclohexane-1,3/2,4-tetrol 
• 61825-76-1 (+/-)-1-bromo-1-deoxyconduritol F 
• 61825-76-1 (+/-)-1-bromo-1-deoxyconduritol B 

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.

Common-intermediate strategy for synthesis of conduritols and inositols via beta-hydroxy cyclohexenylsilanes.

[reaction: see text] Syntheses of conduritols B-D and F and d-(+)-chiro- and neo-inositols from cyclohexenylsilane intermediates are described. The key cyclohexylsilane intermediates 5 and 14 were synthesized by stereoselective olefin dihydroxylation of t

Catalytic behaviour of chloroperoxidase from Caldariomyces fumago in the oxidation of cyclic conjugated dienes

Chloroperoxidase from Caldariomyces fumago has been investigated as a catalyst for the oxidation of cyclic conjugated dienes. The nature of the substituents and the size of the carbocycle affect the enantioselectivity of the enzyme. An unexpected course o

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.

Asymmetric induction of conduritols via AAA reactions: Synthesis of the aminocyclohexitol of hygromycin A

Two synthetic routes towards the construction of the aminocyclohexitol moiety of hygromycin A have been developed based on palladium-catalyzed asymmetric alkylation of conduritol derivatives. A protocol has been established whereby this biologically relev

Facile synthetic routes to all possible enantiomeric pairs of conduritol stereoisomers via efficient enzymatic resolution of conduritol B and C derivatives

matrix presented The first synthesis of all possible enantiomeric pairs of conduritol stereoisomers has been accomplished by efficient enzymatic resolution of conduritol B and C derivatives, followed by oxidation/reduction and the Mitsunobu reaction in st

A norbornyl route to cyclohexitols: Stereoselective synthesis of conduritol-E, allo-inositol, MK 7607 and gabosines

A novel fragmentation sequence within the norbornane system, involving C1-C7 bond scission, provides convenient access to a highly functionalized and versatile cyclohexenoid building block which has been further elaborated to a range of cyclohexitols such as, conduritol E, allo-inositol and gabosine B. Our synthesis of the structure corresponding to gabosine K indicates that the structure of this natural product needs to be revised. (C) 2000 Elsevier Science Ltd.

Practical synthesis of all inositol stereoisomers from myo-inositol

Synthesis of six inositol stereoisomers was successfully carried out via conduritol intermediates prepared from myo-inositol. Dihydroxylation and epoxidation followed by ring opening of the conduritol B, C and F derivatives gave epi-, allo-, muco-, neo-, DL-chiro- and scyllo-inositol. The cis- inositol derivative, which may not be prepared by this approach, was synthesized in 5 steps via 2-O-benzoyl-myo-inositol orthoformate as the key intermediate.

Efficient synthesis of (±)-, (+)-, and (-)-conduritol C via palladium(II)-catalyzed 1,4-diacetoxylation in combination with enzymatic hydrolysis

Palladium-catalyzed diacetoxylation of 5,6-isopropylendioxy-1,3- cyclohexadiene (3) was stereoselective and gave the trans-diacetate 4 (> 94% trans), which after hydrolysis and deprotection, afforded (±)-conduritol. Enzymatic hydrolysis of diacetate 4 produced enantiomerically pure diol (-)- 5 (>99.5% ee) and enantiomerically pure (+)-4 (>99.5% ee). Compounds (-)-5 and (+)-4 were subsequently transformed to (-)- and (+)-conduritol C, respectively.