1043454-52-9Relevant articles and documents
Stereoselective Synthesis and Evaluation of C6-Substituted 5a-Carbasugar Analogues of SL0101 as Inhibitors of RSK1/2
Li, Mingzong,Li, Yu,Ludwik, Katarzyna A.,Sandusky, Zachary M.,Lannigan, Deborah A.,O’Doherty, George A.
, p. 2410 - 2413 (2017/05/12)
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.
Synthesis of carbasugar C-1 phosphates via Pd-catalyzed cyclopropanol ring opening
Shan, Mingde,O'Doherty, George A.
supporting information; experimental part, p. 3381 - 3384 (2009/05/11)
(Chemical Equation Presented) The stereoselective syntheses of 2,3-dideoxy-4-oxo-5a-carba-α-D-rhamnopyanose 1-phosphate, 2,3-dideoxy-5a-carba-α-D-rhamnopyranose 1-phosphate, 5a-carba-α-D- rhamnopyranose 1-phosphate, 5a-carba-α-D-digitoxopyranose 1-phosphate, and 5a-carba-α-L-rhamnopyranose 1-phosphate have been achieved from D-quinic acid. The routes rely upon a Simmons-Smith cyclopropanation and diastereospecific ring opening of cyclopropanol under Pd/C hydrogenation condition to set up the α-methyl ketone. A sequence of diastereoselective reduction, dihydroxylation, and/or Myers' reductive 1,3-rearrangement were used to install the desired stereochemistry.
