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2-deoxyribose as a Rich Source of Chiral 5-carbon Building Blocks

2-deoxyribose as a Rich Source of Chiral 5-carbon Building Blocks

Dengjin Wang, William A Nugent

J Org Chem. 2007 Sep 14;72(19):7307-12.

PMID: 17685659

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP13465117	Indium(II) chloride		13465-11-7	Price

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