123354-99-4

Upstream product

• 4782-75-6 conduritol D 
• 108-24-7 acetic anhydride 
• 133218-73-2 Acetic acid (1S,2S,6R)-2,6-diacetoxy-5-hydroxy-cyclohex-3-enyl ester 
• 171335-61-8 (-)-(1R,2S)-1-acetoxy-2-hydroxycyclohexa-3,5-diene 
• 133319-94-5 (+)-(1S,5S,6S)-1,5,6-triacetoxy-4-oxocyclohex-2-ene 
• 17793-95-2 cis-1,2-dihydrocatechol 
• 94482-74-3 (+)-(1R,2R,4R)-2-endo-cyano-7-oxabicyclo<2.2.1>hept-5-ene-2-exo-yl acetate 
• 84121-00-6 5-exo,6-exo-isopropylidenedioxy-7-oxabicyclo<2.2.1>heptan-2-one 
• 158821-95-5 4t,7t-diacetoxy-(3ar,7ac)-3a,4,7,7a-tetrahydro-benzo[1,3]dioxol-2-one 
• 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 
• 25348-62-3 Acetic acid (3aR,4R,5S,6S,7R,7aS)-5,6,7-triacetoxy-2-thioxo-hexahydro-benzo[1,3]dioxol-4-yl ester 
• 64-19-7 acetic acid 
• 2671-07-0 (+/-)-1r,2c,3t,4c,5t-pentaacetoxy-6t-bromo-cyclohexane 

Downstream Products

• 133319-95-6 (+)-(1R,2R,3S,4S)-1-hydroxy-2,3,4-triacetoxy-5-cyclohexene 
• 133319-93-4 (1S,2R,3S,4S)-5-cyclohexene-1,2,3,4-tetrol 
• 157752-14-2 (1R,2S,3S,6S)-6-Amino-cyclohex-4-ene-1,2,3-triol 
• 183004-31-1 (-)-(1S,2R,3S,4S)-1-benzoyloxy-2,3,4-triacetoxy-5-cyclohexene 
• 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 
• 80226-74-0 (-)-(1R,2S,3S,4R)-1,2,3,4-tetraacetoxy-5-cyclohexene 
• 189389-04-6 (+)-(1S,2R,3R,4S)-1,2,3,4-tetraacetoxy-5-cyclohexene 
• 220564-14-7 (-)-(1R,2R,3S,4R)-1-[(2',2'-dimethyl-4'-tertbutyldimethylsilyloxy)butanoyl]oxy-2,3,4-triacetoxy-5-cyclohexene 
• 949887-64-3 (1R,2R,3S,6S)-6-(pivaloyloxy)cyclohex-4-ene-1,2,3-triyl triacetate 
• 220564-13-6 (1S,2S,3R,6R)-6-(pivaloyloxy)cyclohex-4-ene-1,2,3-triyl triacetate 
• 252316-80-6 (2S,3S)-diacetoxy-(1R,4R)-dihydroxycyclohex-5-ene 

Relevant academic research and scientific papers

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.

Hydroxyhalogenations of acyloxycyclohex-2-enes. Part 3. Iterative 1,2-hydroxyiodination of acetoxycyclohex-2-ene: Preparation of tetraacetyl conduritol D

Compound 22, the tetraacetyl derivative of conduritol D, has been synthesized by repeated hydroxyiodination reactions in nine steps from acetoxycyclohex-2-ene.

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.

Further hydroxyiodination of 1-acetoxycyclohex-2-enes: Preparation of tetraAcetyl conduritol D

1,2-iodohydroxylation of 1-acetoxycyclohex-2-enes has been extrapolated: tetraacetyl Conduritol D may be prepared by iteration of the reaction.