25348-63-4

Basic information

• Product Name: CONDURITOL B TETRAACETATE
• Synonyms: CONDURITOL B TETRAACETATE;(1R,2S,3S,4R)-rel-5-Cyclohexene-1,2,3,4-tetrol 1,2,3,4-Tetraacetate
• CAS NO: 25348-63-4
• Molecular Formula: C₁₄H₁₈O₈
• Molecular Weight: 314.29
• Product Categories: All Inositols;Inositols
• Mol File: 25348-63-4.mol
• Article Data: 14

Chemical Properties

• Melting Point: 75-78°C
• Appearance: /
• Solubility: Chloroform
• CAS DataBase Reference: CONDURITOL B TETRAACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: CONDURITOL B TETRAACETATE(25348-63-4)
• EPA Substance Registry System: CONDURITOL B TETRAACETATE(25348-63-4)

Safety Data

• Hazardous Substances Data: 25348-63-4(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Crystalline Solid

Uses

Conduritol B Tetraacetate (cas# 25348-63-4) is a compound useful in organic synthesis.

Upstream product

• 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 
• 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 
• 31077-18-6 1,2,3,4,5,-penta-O-acetyl-6-bromo-6-deoxy-scyllo-inositol 
• 64-19-7 acetic acid 
• 2671-07-0 (+/-)-1r,2c,3c,4c,5t-pentaacetoxy-6t-bromo-cyclohexane 
• 17793-95-2 (1RS,2RS)-cyclohexa-3,5-diene-1,2-diol 
• 526-87-4 (+/-)-conduritol C 
• 64288-00-2 trans-cyclohexa-3,5-diene-1,2-diyl diacetate 
• 56421-33-1 3t,4c,5c,6t-tetrachloro-cyclohexane-1r,2c-diol 
• 41992-55-6 α-3,4,5,6-Tetrachlorocyclohex-1-ene 
• 526-87-4 conduritol-E 
• 17793-95-2 cis-1,2-dihydrocatechol 
• 127877-55-8 Acetic acid (1R,4S,5S,6S)-6-acetoxy-2,3-dioxa-bicyclo[2.2.2]oct-7-en-5-yl ester 

Downstream Products

• 20021-56-1 (+/-)-1r,2c,3c,4t-tetraacetoxy-cyclohexane 
• 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 
• 526-87-4 (+/-)-Conduritol F 
• 20021-56-1 (+/-)-1D-tetra-O-acetylcyclohexane-1,2,4/3-tetrol 
• 526-87-4 conduritol-E 
• 526-87-4 (+/-)-conduritol C 
• 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 
• 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 
• 949887-64-3 (1R,2R,3S,6S)-6-(pivaloyloxy)cyclohex-4-ene-1,2,3-triyl triacetate 

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

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.

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.