233664-00-1

Basic information

• Product Name: (1R,2R,5R,6S)-5-bromo-6-hydroxycyclohex-3-ene-1,2,3-trimethyl triacetate
• Synonyms: (1R,2R,5R,6S)-5-bromo-6-hydroxycyclohex-3-ene-1,2,3-trimethyl triacetate
• CAS NO: 233664-00-1
• Molecular Weight: 393.232
• Mol File: 233664-00-1.mol

Chemical Properties

• CAS DataBase Reference: (1R,2R,5R,6S)-5-bromo-6-hydroxycyclohex-3-ene-1,2,3-trimethyl triacetate(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R,5R,6S)-5-bromo-6-hydroxycyclohex-3-ene-1,2,3-trimethyl triacetate(233664-00-1)
• EPA Substance Registry System: (1R,2R,5R,6S)-5-bromo-6-hydroxycyclohex-3-ene-1,2,3-trimethyl triacetate(233664-00-1)

Safety Data

• Hazardous Substances Data: 233664-00-1(Hazardous Substances Data)

Relevant articles and documents

Total asymmetric synthesis of doubly branched carba-hexopyranoses and amino derivatives starting from the Diels-Alder adducts of maleic anhydride to furfuryl esters

The Diels-Alder adducts of maleic anhydride to furfuryl esters were reduced into 7-oxabicyclo[2.2.1]hept-5-ene-1,2-exo,3-exo-trimethanol (±)-15 and enantiomerically pure (-)-15 (Scheme 1). The tripivalate of (±)-15 was converted into (1RS,2RS,3RS,4RS,5SR,6SR)-1,5,6- tris(hydroxymethyl)cyclohexane-1,2,3,4-tetrol ((±)-23; Scheme2). Reaction of BBr3 with the triacetate (±)-30 of (±)-15 gave (1RS,2RS,5R,6RS)-5-bromo- 6-hydroxycyclohex-3-ene-1,2,3-trimethyl triacetate ((±)-31) at -78°, and (1RS,2RS,5SR,8SR)-2-endo-hydroxy-6-oxabicylo[3.2.1]oct-3-ene-5,8-dimethyl diacetate ((±)-32) at 0°(Scheme 3). Single-crystal X-ray diffraction of (1RS,2RS,5SR,8SR)-2-acetoxy-6-oxabicyclo[3.2.1]oct-3-ene-5,8-dimethyl diacetate ((±)-33) was carried out. Displacement of bromide (+)-31 (derived from (-)-15) with azide anion gave (+)-38 which was transformed into (+)- (1R,2R,5S,6S)-5-amino-6-hydroxycyclohex-3-ene-1,2,3-trimethanol ((+)-40) (Scheme 4). Reaction of (±)-31 with BBr3 at 0°, followed by azide disubstitution led to (1RS,2RS,5SR,6SR)-5-amino-3-(aminomethyl)-6- hydroxycyclohex-3-ene-1,2-dimethanol ((±)-45). Dihydroxylation of (±)-38 and further transformations gave (1RS,2RS,3SR,4RS,5SR,6RS)-5-amino-1,4,6- trihydroxycyclohexane-1,2,3-trimethanol ((±)-49) and (1RS,2RS,3SR,4RS,5SR,6RS)-2,3-dihydroxy-7-oxabicyclo[4.1.0]heptane-2,3,4- trimethanol ((±)-55) (Schemes 5 and 6). Expoxidation of the 4-nitrobenzoate (±)-61 of (±)-38 allowed the preparation of (1RS,2RS,3SR,4RS,5RS)-5-amino- 1,4-dihydroxycyclohexane-1,2,3-trimethanol ((±)-65) and of (1RS,2RS,3SR,4RS,5SR,6RS)-5-amino-4-hydroxy-7-oxabicyclo[4.1.0]heptane- 1,2,3-trimethanol ((±)-67) (Scheme 7). The new unprotected polyols and aminopolyols were tested for their inhibitory activity toward commercially available glycohydrolases. At 1 mM concentration, 34, 30, and 31% inhibition of β-galactosidase from bovine liver was observed for (+)-40, (±)-65, and (±)-67, respectively.