1043454-72-3Relevant academic research and scientific papers
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.
