4782-75-6

Basic information

• Product Name: CONDURITOL D
• Synonyms: CONDURITOL D;(1R,2R,3S,4S)-rel-5-Cyclohexene-1,2,3,4-tetrol
• CAS NO: 4782-75-6
• Molecular Formula: C₆H₁₀O₄
• Molecular Weight: 146.14
• Product Categories: All Inhibitors;Glycosidase Inhibitors;Inhibitors
• Mol File: 4782-75-6.mol

Chemical Properties

• Boiling Point: 281.926°C at 760 mmHg
• Flash Point: 141.347°C
• Appearance: /
• Density: 1.666g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.693
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: Methanol (Slightly), Water (Slightly)
• CAS DataBase Reference: CONDURITOL D(CAS DataBase Reference)
• NIST Chemistry Reference: CONDURITOL D(4782-75-6)
• EPA Substance Registry System: CONDURITOL D(4782-75-6)

Safety Data

• Hazardous Substances Data: 4782-75-6(Hazardous Substances Data)

Usage

Uses

Conduritol D (cas# 4782-75-6) is a compound useful in organic synthesis.

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

Upstream product

• 743444-57-7 2,2,7,7-tetramethyl-(3ar,5ac,8ac,8bc)-3a,5a,8a,8b-tetrahydro-benzo[1,2-d;3,4-d']bis[1,3]dioxole 
• 219130-50-4 1,4-dihydroxy-5,6-(isopropylidenedioxy)-2-cyclohexene 
• 146830-40-2 C₁₃H₁₉BrO₅ 
• 146830-39-9 C₁₃H₁₇BrO₃ 
• 122596-73-0 (+/-)-O¹,O²;O³,O⁴-diisopropylidene-O⁵,O⁶-bis-(4-nitro-benzenesulfonyl)-epi-inositol 
• 371155-83-8 (3aS,4S,7R,7aS)-3a,4,7,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-4,7-diol dibenzoate 
• 371155-64-5 (3aS,4R,7R,7aS)-3a,4,7,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-4,7-diol 
• 371155-82-7 (3aS,4R,7R,7aS)-3a,4,7,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-4,7-diol 4-monobenzoate 
• 17793-95-2 cis-1,2-dihydrocatechol 
• 143308-52-5 (1α,2β,4β,7α)-3,8,10-trioxa-9,9-dimethyl-tricyclo<5,3,0,0^2,4>doc-5-ene 
• 4381-96-8 (+/-)-(1,3/2,4)-1,2,3,4-tetra-O-acetyl-5-cyclohexene-1,2,3,4-tetrol 
• 4381-96-8 (+/-)-tetraacetylconduritol C 
• 5273-61-0 (5RS,6RS)-5,6-dibromocyclohex-2-ene-1,4-dione 
• 106-51-4 p-benzoquinone 

Downstream Products

• 6090-95-5 conduritol β-epoxide 
• 2975-92-0 d,l-(1,2,3/4)-cyclohexanetetrol 
• 4381-96-8 (+/-)-tetraacetylconduritol C 
• 852045-24-0 (1S,2R,3S,4R,5R,6S)-N-(2,3,4,5,6-pentakis-benzyloxycyclohexyl)octanamide 

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.

A concise synthetic route to the conduritols from pentoses

A short synthetic strategy for preparation of the conduritols is described. The key step employs a zinc-mediated fragmentation of protected methyl 5-deoxy-5-iodo-D-pentofuranosides followed by an allylation of the intermediate aldehyde in the same pot. Th

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

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.

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

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 New Convergent Route to Conduritols A-F from a Common Chiral Building Block

(matrix presented) A diastereocontrolled route to conduritols A-F has been developed starting from a common chiral building block containing an oxabicyclo-[3.2.1]octane framework.

Efficient synthesis of enantiopure conduritols by ring-closing metathesis

Two short synthetic approaches to enantiopure conduritols are described starting from the chiral pool. In both cases, the cyclohexene ring is assembled via ring-closing olefin metathesis. The terminal diene precursers for the metathesis reaction are prepared either from octitols or from tartaric acids. The former route involves a new method for selective bromination of the primary positions in long-chain carbohydrate polyols. Subsequent reductive elimination with zinc then generates the diene. The latter route uses a highly diastereoselective addition of divinylzinc to tartaric dialdehydes for preparation of the dienes.