Synthesis of deoxytetrahydrouridine.
Synthesis of deoxytetrahydrouridine.
复制标题
脱氧四氢尿苷的合成。
DOI：
10.1021/jo802599v
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发表时间：
2009
期刊：
影响因子：
--
通讯作者：
Sturla,ShanaJ
中科院分区：
文献类型：
--
作者：
Norton,Jolanna;Matsuo,Hiroshi;Sturla,ShanaJ
The α-hydroxyamido functionality of 2′-deoxytetrahydrouridine (dTHU) makes this seemingly simple and generally useful compound difficult to obtain. Reported synthetic strategies produce extremely poor yields and multiple products, and full characterization data is not available. Described herein is a two-step approach for synthesizing dTHU in increased yields and purity; stability concerns are also addressed. Catalytic reduction (5% Rh/alumina) of 2′-deoxyuridine, followed by reduction with sodium borohydride as a limiting reagent, produces dTHU and limits formation of side products. Evidence was obtained for formation of a methoxy-substituted analogue during purification. By this strategy, dTHU of >95% purity can be obtained in 40% yield on a 150 mg scale.
