2-deoxyribose as a rich source of chiral 5-carbon building blocks.
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.
Wang
Dengjin
D
Process Research and Development, Bristol-Myers Squibb Company, Princeton, NJ 08543, USA. dengjin.wang@bms.com
Nugent
William A
WA
D000447:Aldehydes / Q000138:chemical synthesis*; D002264:Carboxylic Acids / Q000138:chemical synthesis*; D002384:Catalysis; D003855:Deoxyribose / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000447:Aldehydes; D002264:Carboxylic Acids; D006027:Glycosides; D007783:Lactones; D003855:Deoxyribose