Stereoselective synthesis of 1-C-alkyl iminogalactitol derivatives, potential chaperones for galactosidase-linked LSDs: a real challenge

Autor:	Anna Biela-Banaś, Estelle Gallienne, Olivier R. Martin, Sophie Front
Rok vydání:	2014
Předmět:	chemistry.chemical_classification Derivative (finance) Chemistry Organic Chemistry Drug Discovery Stereoselectivity Lysosomal storage disorders Epimer Biochemistry Deoxygenation Combinatorial chemistry Alkyl
Zdroj:	Tetrahedron Letters. 55:838-841
ISSN:	0040-4039
Popis:	1-C-Alkyl iminogalactitol derivatives are highly desirable target compounds as potential pharmacological chaperones for the treatment of galactosidase-linked lysosomal storage disorders (LSDs). The synthesis of such compounds from d-galactose by a C-1 chain extension process by way of an open-chain 6-amino d-gulo nonulose intermediate was complicated by unexpected deoxygenation reactions leading to 3-deoxy iminogalactitol derivatives and epimers; an alternative, stereocontrolled synthesis from an l-tagatose derivative by C-6 chain-extension was therefore developed, which involved addition of organometallic reagents onto t-butanesulfinylimine intermediates in the key step.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::c3044ec634fef44165fdda9912fda20e https://doi.org/10.1016/j.tetlet.2013.12.024 Zobrazit plný text záznamu Full Text from ScienceDirect