Convenient approaches to synthesis of furanoid sugar-aza-crown ethers from C-ribosyl azido aldehyde via a reductive amination/amidation

Yu-Chi Hsieh; Jiun-Ly Chir; Wei Zou; Hsiu-Han Wu; An-Tai Wu

doi:10.1016/j.carres.2009.03.008

Convenient approaches to synthesis of furanoid sugar-aza-crown ethers from C-ribosyl azido aldehyde via a reductive amination/amidation

Carbohydr Res. 2009 May 26;344(8):1020-3. doi: 10.1016/j.carres.2009.03.008. Epub 2009 Mar 12.

Authors

Yu-Chi Hsieh¹, Jiun-Ly Chir, Wei Zou, Hsiu-Han Wu, An-Tai Wu

Affiliation

¹ Department of Chemistry, National Changhua University of Education, Changhua 50058, Taiwan.

PMID: 19362710
DOI: 10.1016/j.carres.2009.03.008

Abstract

A short and highly efficient route to the alpha-anomer of a furanoid sugar-aza-crown ether was developed by a one-pot reductive amination of an alpha-anomer C-ribosyl azido aldehyde. In addition, the beta-anomer furanoid sugar-aza-crown ether was synthesized from a linear disaccharide precursor via amidation and then followed by microwave-assisted amide reduction.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aldehydes / chemistry*
Amination
Aza Compounds / chemical synthesis*
Aza Compounds / chemistry*
Crown Ethers / chemical synthesis*
Crown Ethers / chemistry*
Magnetic Resonance Spectroscopy
Molecular Structure

Substances

Aldehydes
Aza Compounds
Crown Ethers