2-deoxyribose as a rich source of chiral 5-carbon building blocks |
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Authors: | Wang Dengjin Nugent William A |
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Affiliation: | Process Research and Development, Bristol-Myers Squibb Company, Princeton, NJ 08543, USA. dengjin.wang@bms.com |
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Abstract: | We have developed concise routes to a number of useful chiral 5-carbon synthetic building blocks using readily available O-1-methyl-2-deoxyribose as starting material. Novel transformations include the use of indium triflate to catalyze the oxidation of a methyl furanoside to the corresponding lactone with MCPBA and the Vasella-type fragmentation of a 5-iodo furanoside using chromium(II) chloride when zinc proved ineffective. In addition, 3,4-disubstituted piperidine derivatives were prepared without hydroxyl group protection via a simple reductive amination reaction. |
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