594858-32-9

Basic information

• Product Name: 5-Cyclohexene-1,2,3,4-tetrol, tetraacetate, (1R,2R,3R,4R)-
• CAS NO: 594858-32-9
• Molecular Formula: C14H18O8
• Molecular Weight: 314.292
• Mol File: 594858-32-9.mol

Chemical Properties

• CAS DataBase Reference: 5-Cyclohexene-1,2,3,4-tetrol, tetraacetate, (1R,2R,3R,4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Cyclohexene-1,2,3,4-tetrol, tetraacetate, (1R,2R,3R,4R)-(594858-32-9)
• EPA Substance Registry System: 5-Cyclohexene-1,2,3,4-tetrol, tetraacetate, (1R,2R,3R,4R)-(594858-32-9)

Safety Data

• Hazardous Substances Data: 594858-32-9(Hazardous Substances Data)

Upstream product

• 188839-30-7 (3aS,4R,5R,6R,7R,7aS)-4,7-Bis-(tert-butyl-diphenyl-silanyloxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-5,6-diol 
• 188839-35-2 D-1,6-O-(1-methylethylidene)-2,5-bis-O-(phenylmethyl)-allo-inositol 
• 90126-16-2 2,5-di-O-benzyl-3,4-O-isopropylidene-D-mannitol 
• 4381-96-8 (+/-)-1,2,3,4-tetra-O-acetylconduritol E 
• 4782-75-6 conduritol D 
• 17793-95-2 cis-1,2-dihydrocatechol 
• 108-24-7 acetic anhydride 
• 170210-90-9 Acetic acid (1R,4R,5S,6S)-4-acetoxy-5,6-dibromo-cyclohex-2-enyl ester 
• 191793-10-9 Acetic acid (1R,2R,5R,6R)-2,6-diacetoxy-5-hydroxy-cyclohex-3-enyl ester 
• 171335-61-8 (-)-(1R,2S)-1-acetoxy-2-hydroxycyclohexa-3,5-diene 

Relevant articles and documents

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.

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.