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 lacto...

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Bibliographic Details
Published in:Journal of organic chemistry 2007-09, Vol.72 (19), p.7307-7312
Main Authors: Wang, Dengjin, Nugent, William A
Format: Article
Language:English
Subjects:
Aldehydes - chemical synthesis
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Carboxylic Acids - chemical synthesis
Catalysis
Chemistry
Deoxyribose - chemistry
Exact sciences and technology
Glycosides - chemistry
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Lactones - chemical synthesis
Organic chemistry
Oxidation-Reduction
Preparations and properties
Stereoisomerism
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Summary: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-disubstitued piperidine derivatives were prepared without hydroxyl group protection via a simple reductive amination reaction.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0712143