676543-78-5

Basic information

• Product Name: 2,3-Dioxabicyclo[2.2.2]oct-7-en-5-ol,acetate,(1R,4R,5R)-rel-(9CI)
• Synonyms: 2,3-Dioxabicyclo[2.2.2]oct-7-en-5-ol,acetate,(1R,4R,5R)-rel-(9CI)
• CAS NO: 676543-78-5
• Molecular Formula: C8H10O4
• Molecular Weight: 170.1626
• Product Categories: METHOXY
• Mol File: 676543-78-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,3-Dioxabicyclo[2.2.2]oct-7-en-5-ol,acetate,(1R,4R,5R)-rel-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Dioxabicyclo[2.2.2]oct-7-en-5-ol,acetate,(1R,4R,5R)-rel-(9CI)(676543-78-5)
• EPA Substance Registry System: 2,3-Dioxabicyclo[2.2.2]oct-7-en-5-ol,acetate,(1R,4R,5R)-rel-(9CI)(676543-78-5)

Safety Data

• Hazardous Substances Data: 676543-78-5(Hazardous Substances Data)

Upstream product

• 1165952-92-0 cyclohexa-1,4-diene 
• 108-05-4 vinyl acetate 
• 75-36-5 acetyl chloride 

Downstream Products

• 676543-81-0 (1R,2R,5R)-(+)-2,5-bis(acetyloxy)cyclohex-3-en-1-yl acetate 

Relevant articles and documents

Stereospecific synthesis of a dl-gala-aminoquercitol derivative

A new aminoquercitol derivative was synthesized starting from 1,4-cyclohexadiene. Photooxygenation of cyclohexa-1,4-diene afforded anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-yl hydroperoxide as the main product. The formed hydroperoxy endoperoxide was reduced with LiAlH4 to produce anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol. Protection of alcohol with acetyl chloride followed by reduction of the endoperoxide with thiourea, and then palladium-catalyzed ionization/cyclization reaction gave an oxazolidinone derivative. Hydrolysis of the oxazolidinone ring and acetylation gave an amino compound. Oxidation of the double bond in the amino compound with OsO4 followed by acetylation gave the amino tetraacetate and removal of the acetate groups furnished the desired aminoquercitol whose exact configuration was determined by X-ray diffraction analysis.

Resolution of (±)-anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol via Candida cylindracea lipase: Synthesis of (-)- and (+)-proto-quercitol

Photooxygenation of cyclohexa-1,4-diene afforded anti-2,3-dioxabicyclo[2.2. 2]oct-7-en-5-yl hydroperoxide. The hydroperoxy endoperoxide was reduced with dimethylsulfide-titanium tetraisopropoxide to produce (±)-anti-2,3- dioxabicyclo[2.2.2]oct-7-en-5-ol. The highly efficient enantioselective resolution of the racemic (±)-anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol was accomplished with Candida cylindracea lipase (CCL) to produce the enantiomerically enriched alcohol and the corresponding acetate: The cleavage of the peroxide linkage by thiourea followed by the oxidation of the double bond with OsO4 resulted in the formation of (-)-proto-quercitol and (+)-proto-quercitol, respectively.