93292-92-3

Basic information

• Product Name: (-)-(1R,4S)-(1,4-dihydroxy-cyclopent-2-enyl)-acetic acid t-butyl ester
• CAS NO: 93292-92-3
• Molecular Weight: 214.262
• Mol File: 93292-92-3.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (-)-(1R,4S)-(1,4-dihydroxy-cyclopent-2-enyl)-acetic acid t-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-(1R,4S)-(1,4-dihydroxy-cyclopent-2-enyl)-acetic acid t-butyl ester(93292-92-3)
• EPA Substance Registry System: (-)-(1R,4S)-(1,4-dihydroxy-cyclopent-2-enyl)-acetic acid t-butyl ester(93292-92-3)

Safety Data

• Hazardous Substances Data: 93292-92-3(Hazardous Substances Data)

Upstream product

• 540-88-5 acetic acid tert-butyl ester 
• 59995-47-0 4-Hydroxycyclopent-2-enone 
• 59995-47-0 (S)-4-hydroxycyclopent-2-en-1-one 

Downstream Products

• 85700-43-2 5E,7E-Clavulone II 
• 93292-93-4 [(1S,4S)-1,4-Bis-(tetrahydro-pyran-2-yloxy)-cyclopent-2-enyl]-acetic acid tert-butyl ester 

Relevant articles and documents

A stereo- and enantioselective approach to clavulones from tricyclodecadienone using flash vacuum thermolysis

The stereo- and enantioselective synthesis of clavulones 6 and their analogues 48 is described. γ-Hydroxycyclopentenones (-)-13 and 44, which are key intermediates in this approach, are obtained from enantiopure endo-tricyclo[5.2.1.02,6]decadienones (+)-14 and (+)-20 in 6 and 8 steps, respectively. Crucial steps are the reductive epoxy ring opening in compounds (+)-25 and 39 to give the corresponding diols (+)-27 and 40, and the thermal cycloreversion of tricyclodecenones (+)-27 and 41, using the technique of flash vacuum thermolysis (FVT). The synthesis of enantiopure (-)-13 represents a formal total synthesis of clavulones 6. The synthesis of vlavulone analogues (-)-48E and (-)-48Z (X = CH2OH) is completed by condensation of 44 with aldehyde 45 followed by elimination of water and removal of the protective THP-group.