Preparation of Both C5′ Epimers of 5′-C-Methyladenosine: Reagent Control Trumps Substrate Control

被引：23

作者：

Bligh, Cavan M. ^{[1
]}

Anzalone, Luigi ^{[1
]}

Jung, Young Chun ^{[1
]}

Zhang, Yuegang ^{[1
]}

Nugent, William A. ^{[1
]}

机构：

[1] Vertex Pharmaceut Inc, Boston, MA 02210 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 07期

关键词：

ASYMMETRIC TRANSFER HYDROGENATION; LIGAND BIFUNCTIONAL CATALYSIS; POTENTIAL ANTICANCER AGENTS; CARBONYL-COMPOUNDS; ADENOSINE-DEAMINASE; AROMATIC KETONES; TARTARIC ACID; NUCLEOSIDES; COMPLEXES; REDUCTION;

D O I：

10.1021/jo500089t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Adenosine-derived ketone 5 was subjected to Noyori asymmetric transfer hydrogenation (ATH) using aqueous sodium formate as a stoichiometric reductant. Despite the well-known sensitivity of ATH to stereoelectronic effects from a contiguous stereogenic center, the 5' stereochemistry was overwhelmingly controlled by the chirality of the catalyst. Both the (5'S,4'R) and the (5'R,4'R) diastereomers could be prepared selectively in good yields. An efficient three-step route that provides ketone 5 in 75% overall yield was developed.

引用

页码：3238 / 3243

页数：6

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