952330-22-2

Basic information

• Product Name: (4S,5R)-4-hydroxy-5-propylcyclohex-2-enone
• Synonyms: (4S,5R)-4-hydroxy-5-propylcyclohex-2-enone
• CAS NO: 952330-22-2
• Molecular Weight: 154.209
• Mol File: 952330-22-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (4S,5R)-4-hydroxy-5-propylcyclohex-2-enone(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,5R)-4-hydroxy-5-propylcyclohex-2-enone(952330-22-2)
• EPA Substance Registry System: (4S,5R)-4-hydroxy-5-propylcyclohex-2-enone(952330-22-2)

Safety Data

• Hazardous Substances Data: 952330-22-2(Hazardous Substances Data)

Upstream product

• 121651-99-8 (4S,5R)-4,5-O-isopropylidenedioxycyclohex-2-en-1-one 
• 101917-46-8 (3aS,4R,6R,7aR)-6-Hydroxymethyl-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-4,6-diol 
• 32384-42-2 (1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone 

Relevant articles and documents

Stereoselective Synthesis and Evaluation of C6-Substituted 5a-Carbasugar Analogues of SL0101 as Inhibitors of RSK1/2

A convergent synthesis of 5a-carbasugar analogues of the n-Pr-variant of SL0101 is described. The analogues were synthesized in an effort to find compounds with potent in vivo efficacy in the inhibition of p90 ribosomal s6 kinase (RSK1/2). The synthesis derived the desired C-4 L-rhamnose stereochemistry from quinic acid and used a highly selective cuprate addition, NaBH4 reduction, Mitsunobu inversion, and alkene dihydroxylation to install the remaining stereochemistry. A Pd-catalyzed cyclitolization stereoselectively installed the aglycon at the anomeric position. The analogues were evaluated as RSK1/2 inhibitors and found to have 3- to 6-fold improved activity.