De Novo Synthesis of Sugar-Aza-Crown Ethers via a Domino Staudinger Aza-Wittig Reaction
- 17 March 2006
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 71 (8), 3295-3298
- https://doi.org/10.1021/jo052489q
Abstract
A short and highly efficient route to sugar-aza-crown (SAC) ethers has been developed. The key step of the transformation is a one-pot cyclodimerization of C-glycosyl azido aldehydes via a domino Staudinger aza-Wittig reaction. This process allows the preparation of various orthogonally protected SAC ethers, from both α- and β-C-glycosyl azido aldehydes.Keywords
This publication has 10 references indexed in Scilit:
- Highly Convergent Synthesis of C3- or C2-Symmetric Carbohydrate MacrocyclesOrganic Letters, 2005
- Synthesis of Orthogonally Protected Cyclic Homooligomers from Sugar Amino AcidsThe Journal of Organic Chemistry, 2005
- Synthetic Studies on Macroviracin A: A Rapid Construction of C42 Macrocyclic Dilactone Corresponding to the CoreThe Journal of Organic Chemistry, 2004
- Phase-transfer catalyzed asymmetric epoxidation of chalcones using chiral crown ethers derived from d-glucose, d-galactose, and d-mannitolTetrahedron: Asymmetry, 2004
- Crown Ethers: Sensors for Ions and Molecular Scaffolds for Materials and Biological ModelsChemical Reviews, 2004
- Synthesis of Readily Modifiable Cyclodextrin Analogues via Cyclodimerization of an Alkynyl−Azido TrisaccharideJournal of the American Chemical Society, 2004
- Structure Assignment, Total Synthesis, and Antiviral Evaluation of Cycloviracin B1Journal of the American Chemical Society, 2003
- Dependence of Ring Size on Conditions in Cyclization of 4-Methylaminobenzoic Acid by DichlorotriphenylphosphoraneHETEROCYCLES, 2003
- Palladium and Raney Nickel Catalyzed Methanolic Cleavage of Stable Borane−Amine ComplexesOrganic Letters, 2001
- Sixty years of staudinger reactionTetrahedron, 1981