1- C-Alkyl imino- d-xylitol and - l-arabinitol derivatives obtained via nucleophilic addition to pentose-derived N- tert-butanesulfinyl imines: sugar- versus chiral auxiliary-induced stereoselectivity

Farah Oulaïdi,Estelle Gallienne,Philippe Compain,Olivier R Martin

doi:10.1016/j.tetasy.2011.02.024

1- C-Alkyl imino- d-xylitol and - l-arabinitol derivatives obtained via nucleophilic addition to pentose-derived N- tert-butanesulfinyl imines: sugar- versus chiral auxiliary-induced stereoselectivity

Farah Oulaïdi, Estelle Gallienne + Show 2 more

https://doi.org/10.1016/j.tetasy.2011.02.024

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Journal: Tetrahedron: Asymmetry	Publication Date: Mar 1, 2011
Citations: 14

Affiliation: University of Orléans, Institute of Organic and Analytical Chemistry, French National Centre for Scientific Research, Laboratory of Design and Application of Bioactive Molecules, University of Strasbourg, Laboratory of Organic Synthesis

#Tert-butanesulfinyl Imines #Sugar Moiety + Show 7 more

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Abstract

The stereoselective synthesis of 1- C-alkyl iminosugars in the d- xylo and l- arabino series as potential drugs for the treatment of lysosomal diseases has been achieved. The key step involves nucleophilic addition to pentodialdofuranose-derived imines generated using enantiopure tert-butanesulfinamide. Depending on the pentofuranose configuration and structure, the stereoselectivity of this reaction was found to be controlled either by the sugar moiety or by the stereogenic sulfur center.

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