Practical synthesis of 1′-substituted Tubercidin C-nucleoside analogs

Autor:	Evangelos Aktoudianakis, Choung U. Kim, Oliver L. Saunders, Jie Xu, Sammy Metobo, Thomas Butler, Aesop Cho
Rok vydání:	2012
Předmět:	Chemistry Stereochemistry Organic Chemistry Convergent synthesis Ether Biochemistry Tubercidin chemistry.chemical_compound Nucleophile Drug Discovery Ribose Chelation Stereoselectivity C nucleosides
Zdroj:	Tetrahedron Letters. 53:484-486
ISSN:	0040-4039
Popis:	Several 1′-substituted analogs of Tubercidin C-nucleosides were prepared using a highly convergent synthesis. Good to high diastereoselectivity was achieved using a variety of nucleophiles targeting the 1′-position. The source for this stereoselectivity is herein proposed. It is thought to be attributed to a temperature-dependent chelation of the incoming nucleophile to either the 2′- or 3′-benzyloxy ether of the ribose core.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::6c9f48224d1b9d6c0861de95d892fa06 https://doi.org/10.1016/j.tetlet.2011.11.055 Zobrazit plný text záznamu Full Text from ScienceDirect