高效制备 2,4-二氨基嘧啶核苷：赖氨啶和胍啶的全合成。

Efficient preparation of 2,4-diaminopyrimidine nucleosides: total synthesis of lysidine and agmatidine.

机构信息

Pharmaceutical Sciences Division, School of Pharmacy, University of Wisconsin-Madison, Madison, Wisconsin 53705, United States.

出版信息

Org Lett. 2012 Aug 17;14(16):4118-21. doi: 10.1021/ol301769j. Epub 2012 Jul 30.

DOI:10.1021/ol301769j

PMID:22845013

Abstract

An efficient route for the synthesis of 2,4-diaminopyrimidine ribosides from cytidine is described consisting of six steps with overall yields >50% and only one chromatographic step. The key amine addition step utilizes LiCl and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) to ensure clean conversion to a single tautomeric product. This route has been used to prepare the modified tRNA nucleosides lysidine and agmatidine in quantities suitable for structural characterization.

摘要

描述了一种从胞苷合成 2,4-二氨基嘧啶核苷的有效途径，包括六个步骤，总收率超过 50%，仅需一步色谱分离。关键的胺加成步骤利用 LiCl 和 1,8-二氮杂二环[5.4.0]十一碳-7-烯（DBU），以确保单一互变异构产物的干净转化。该路线已用于制备适合结构表征的修饰 tRNA 核苷赖氨酸和胍丁啶。