通过钯催化的N-糖基化反应从头不对称合成同型腺苷。
De novo asymmetric synthesis of homoadenosine via a palladium-catalyzed N-glycosylation.
作者信息
Guppi Sanjeeva R, Zhou Maoquan, O'Doherty George A
机构信息
Department of Chemistry, West Virginia University, Morgantown, 26506, USA.
出版信息
Org Lett. 2006 Jan 19;8(2):293-6. doi: 10.1021/ol052664p.
Abstract
[reaction: see text] A highly stereoselective synthesis of l-2-deoxy-beta-ribo-hexopyranosyl nucleosides from 6-chloropurine and Boc-protected pyranone has been developed. Our approach relies on the iterative application of a palladium-catalyzed N-glycosylation, diastereoselective reduction, and reductive 1,3-transposition. This strategy is amenable to prepare various natural and unnatural hexopyranosyl nucleosides analogues.
摘要
[反应：见正文] 已开发出一种从6-氯嘌呤和Boc保护的吡喃酮高度立体选择性合成l-2-脱氧-β-核糖己吡喃糖基核苷的方法。我们的方法依赖于钯催化的N-糖基化、非对映选择性还原和还原性1,3-转位的迭代应用。该策略适用于制备各种天然和非天然己吡喃糖基核苷类似物。
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