129829-60-3

Basic information

• Product Name: 5-Cyclohexene-1,2,3,4-tetrol, tetraacetate, (1S,2S,3S,4R)-
• CAS NO: 129829-60-3
• Molecular Formula: C14H18O8
• Molecular Weight: 314.292
• Mol File: 129829-60-3.mol
• Article Data: 18

Chemical Properties

• CAS DataBase Reference: 5-Cyclohexene-1,2,3,4-tetrol, tetraacetate, (1S,2S,3S,4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Cyclohexene-1,2,3,4-tetrol, tetraacetate, (1S,2S,3S,4R)-(129829-60-3)
• EPA Substance Registry System: 5-Cyclohexene-1,2,3,4-tetrol, tetraacetate, (1S,2S,3S,4R)-(129829-60-3)

Safety Data

• Hazardous Substances Data: 129829-60-3(Hazardous Substances Data)

Upstream product

• 106-51-4 p-benzoquinone 
• 145047-67-2 Acetic acid (1R,2S,3S,4R,5S,6R)-4-acetoxy-2,3-dibromo-5,6-dihydroxy-cyclohexyl ester 
• 112212-81-4 (+/-)-(1S,2R,3R,4S)-1,4-diacetoxy-2,3-dibromocyclohex-5-ene 
• 69945-44-4 (1RS,2SR,3RS,4RS)-2,3-dibromocyclohex-5-ene-1,4-diol 
• 5273-61-0 (5RS,6RS)-5,6-dibromocyclohex-2-ene-1,4-dione 
• 123155-30-6 (-)-(1R,2R,4R,5S,6R)-2-endo-cyano-5-exo,6-exo-dihydroxy-7-oxabicyclo<2.2.1>hept-2-exo-yl-acetate 
• 123155-31-7 (-)-(1R,2R,4R,5R,6S)-5-exo,6-exo-bis<<(tert-butyl)dimethylsilyl>oxy>-2-endo-cyano-7-oxabicyclo<2.2.1>hept-2-exo-yl acetate 
• 94482-74-3 (+)-(1R,2R,4R)-2-endo-cyano-7-oxabicyclo<2.2.1>hept-5-ene-2-exo-yl acetate 
• 108-24-7 acetic anhydride 
• 2671-07-0 (+/-)-1r,2c,3c,4c,5t-pentaacetoxy-6t-bromo-cyclohexane 
• 64-19-7 acetic acid 
• 18376-35-7 (1α,2β,3α,4β,5β,6β)-1,2-dibromo-3,4,5,6-tetraacetoxycyclo-hexane 
• 64288-00-2 trans-cyclohexa-3,5-diene-1,2-diyl diacetate 
• 526-87-4 (+/-)-conduritol C 

Downstream Products

• 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 
• 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 
• 347377-79-1 C₂₈H₂₃NO₆ 
• 347377-76-8 (+)-(1S,2R,3R,4S)-1,4-Dibenzoyloxy-2-(N-benzyl)carbamyl-5-cyclohexene-3-ol 
• 347377-80-4 C₂₈H₂₅NO₈ 
• 347377-82-6 C₂₉H₂₅NO₈ 
• 347377-78-0 C₂₉H₂₄F₃NO₉S 
• 6090-95-5 conduritol β-epoxide 
• 29267-04-7 hexa-O-acetyl allo-inositol 
• 20097-40-9 hexa-O-acetyl-neo-inositol 

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.

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