4381-96-8

Basic information

• Product Name: (+/-)-tetraacetylconduritol C
• CAS NO: 4381-96-8
• Molecular Weight: 314.292
• Mol File: 4381-96-8.mol

Chemical Properties

• CAS DataBase Reference: (+/-)-tetraacetylconduritol C(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-tetraacetylconduritol C(4381-96-8)
• EPA Substance Registry System: (+/-)-tetraacetylconduritol C(4381-96-8)

Safety Data

• Hazardous Substances Data: 4381-96-8(Hazardous Substances Data)

Upstream product

• 31077-18-6 1,2,3,4,5,-penta-O-acetyl-6-bromo-6-deoxy-scyllo-inositol 
• 55990-84-6 Acetic acid (1R,2S,5R,6S)-5-acetoxy-7-oxa-bicyclo[4.1.0]hept-3-en-2-yl ester 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 69945-44-4 (1RS,2SR,3RS,4RS)-2,3-dibromocyclohex-5-ene-1,4-diol 
• 87-89-8 D-myo-inositol 
• 17793-95-2 (1RS,2RS)-cyclohexa-3,5-diene-1,2-diol 
• 135505-67-8 endo-cis-7-oxabicyclo<2.2.1>hept-5-ene-2,3-diol diacetate 
• 56421-33-1 3t,4c,5c,6t-tetrachloro-cyclohexane-1r,2c-diol 
• 526-87-4 conduritol-E 
• 112212-81-4 (+/-)-(1S,2R,3R,4S)-1,4-diacetoxy-2,3-dibromocyclohex-5-ene 
• 106-51-4 p-benzoquinone 
• 526-87-4 (+/-)-conduritol C 
• 64288-00-2 trans-cyclohexa-3,5-diene-1,2-diyl diacetate 

Downstream Products

• 135346-51-9 Acetic acid (1S,2S,5R,6S)-5,6-diacetoxy-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-cyclohex-3-enyl ester 
• 526-87-4 (+/-)-Conduritol B 
• 144705-48-6 (+/-)-(1,3,4/2)-1,2,3-Tri-O-acetyl-4-bromo-5-cyclohexene-1,2,3-triol 
• 144705-48-6 (+/-)-(1,3/2,4)-1,2,3-Tri-O-acetyl-4-bromo-5-cyclohexene-1,2,3-triol 
• 1254-38-2 inositol peracetate 
• 189389-04-6 (+)-(1S,2R,3R,4S)-1,2,3,4-tetraacetoxy-5-cyclohexene 
• 220564-13-6 (1S,2S,3R,6R)-6-(pivaloyloxy)cyclohex-4-ene-1,2,3-triyl triacetate 
• 220564-14-7 (-)-(1R,2R,3S,4R)-1-[(2',2'-dimethyl-4'-tertbutyldimethylsilyloxy)butanoyl]oxy-2,3,4-triacetoxy-5-cyclohexene 
• 6090-95-5 conduritol β-epoxide 
• 526-87-4 (+/-)-Conduritol F 
• 20021-56-1 (+/-)-1D-tetra-O-acetylcyclohexane-1,2,4/3-tetrol 
• 526-87-4 conduritol-E 
• 182075-57-6 1,2,3,4-tetra-O-acetylconduritol E 
• 191793-10-9 Acetic acid (1R,2R,5R,6R)-2,6-diacetoxy-5-hydroxy-cyclohex-3-enyl ester 

Relevant articles and documents

Synthesis of both enantiomers of conduritol C tetraacetate and of meso-conduritol D tetraacetate by oxidation of benzoquinone bis(ethylene acetal)

Epoxidation of p-benzoquinone bis(ethylene acetal) (1) with m-chloroperbenzoic acid or hydrogen peroxide/benzonitrile afforded corresponding monoepoxide 2, which was converted into p-benzoquinone mono(ethylene acetal) monoepoxide 5 with perchloric acid. D

Stereoselective synthesis of myo-, neo-, L-chiro, D-chiro, allo-, scyllo-, and epi-inositol systems via conduritols prepared from p-benzoquinone

A practical route is described for the flexible preparation of a wide variety of inositol stereoisomers and their polyphosphates. The potential of this approach is demonstrated by the synthesis of myo-, L-chiro-, D-chiro-, epi-, scyllo-, allo-, and neo-inositol systems. Optically pure compounds in either enantiomeric form can be prepared from p-benzoquinone via enzymatic resolution of a derived conduritol B key intermediate. High-performance anion-exchange chromatography with pulsed amperometric detection permits inositol stereoisomers to be resolved and detected with high sensitivity. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Synthesis of haloconduritols from an endo-cycloadduct of furan and vinylene carbonate

A method for preparing haloconduritols having a conduritol-A construction is described. A mixture of endo- and exo-cycloadduct derivatives prepared from the Diels-Alder reaction of furan and vinylene carbonate was converted into diacetate derivatives by hydrolysis (K2CO3/MeOH) followed by acetylation (Ac2O/pyridine). Boron trihalide (BBr3 or BCl3)-assisted ring-opening of the endo-diacetate in CH2Cl2 at -78°C gave (1α,2α,3β,6β)-6-halogeno-4-cyclohexene-1,2,3-triol 1,2-diacetate from which the corresponding triacetate was prepared by acetylation (AcCl). trans-Esterification of the triacetate (MeOH/HCl) afforded (1α,2α,3β,6β)-6-halogeno-4-cyclohexene-1,2,3-triol (X=Br or Cl). BF3-Assisted ring-opening of the endo-diacetate in CH2Cl2 gave (1α,2α,3β,6β)-6-chloro-4-cyclohexene-1,2,3-triol 1,2-diacetate by means of halogen exchange.

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

From cycloolefins to chiral, polyfunctionalized linear C6/C12 building blocks - Biocatalysis, (-)-conduramine E

1,4-Cyclohexadiene is the starting material for the expeditious synthesis of the 1S2S3S4R- and 1R2R3R4S-epoxy-cyclohexene-1,4-diol monoacetates through enzyme-catalyzed hydrolysis and transesterification, respectively. The absolute configurations are established by correlation of (-)-10 and known (+)-conduramine E. Ozonation and functional group manipulation open access to fully protected, polyfunctionalized C6-aldehydes whose reductive coupling to C2-symmetrical C12 building blocks is being explored. (C) 2000 Elsevier Science Ltd.

An efficient enzymatic preparation of (+)- and (-)-conduritol E, a cyclitol with C2 symmetry

Lypozyme IM (immobilised lipase from Mucor miehei) catalyses the enantiomeric alcoholysis of tetraacetylconduritol E (±)-2 to give enantiopure (1R,2R,3R,4R)-tetrahydroxycyclohex-5-ene (-)-1, and the unreacted ester (1S,2S,3S,4S)-tetraacetyloxycyclohex-5-ene, (+)-2. The latter was transformed by basic hydrolysis into (+)-1 in high yield and 95% ee. Selective amination of partial ester (-)-3, obtained by short alcoholysis of (±)-2, furnished the previously unreported conduramine F-4, (-)-4.

Stereochemical observations on the bromate induced monobromopentahydroxylation of benzene by catalytic photoinduced charge transfer osmylation. A concise synthesis of (±)-pinitol

The use of lower temperatures in the title reaction favours the formation of the neo diastereoisomer of the deoxybromoinositol whose diisopropylidene derivative can be converted in three steps to (±)-pinitol.

Improved preparation of (±)-(1,3/2,4)-5-cyclohexene-1,2,3,4-tetrol [(±)-conduritol-B] and its reaction with hydrobromic and hydrochloric acid; synthesis and characterisation of some (±)-1-deoxy-1-halo- and (±)-1,4-dideoxy-1,4-dihalo-conduritols

An active-site directed, covalent inhibitor of α-glucosidases is the mixture of (±)-1-bromo (1,3/2,4)-5-cyclohexene-2,3,4-triol [(±)-1-bromo-1-deoxyconduritol F] (2), formed on treatment of (±)-conduritol-B (3) with hydrogen bromide and termed 'bromo cond

A novel synthesis of Conduritol-C and Conduritol-E via p-benzoquinone

A new and sterospecific synthesis for Conduritol-C 8 and Conduritol-E 13a has been developed starting from p-benzoquinone 1. 1,4-oxygen functionalities were introduced in both synthesis by the reduction of dibromo p-benzoquinone 2 with NaBH4. 2

Catalytic One-Pot Osmylation of Cyclohexadienes: Stereochemical and Conformational Studies of the Resulting Polyols

Catalytic double osmylation is described for a series of cyclohexadienes in acetone/H2O in the presence of the co-oxidant N-methylmorpholine N-oxide (NMO).The formation of polyols occurred stereospecifically with cyclohexadienes 3, 7, and 11a, leading thereby to tetrols 5a, and 9a and to allo-inositol (14a), respectively.To the contrary, trans-cyclohexadiene-diol 15a gave a mixture of the stereoisomeric inositols 18a (epi), 19a (neo), and 20a (chiro).High-field NMR let to clearcut conformational analyses of the polyhydroxylated derivatives.