Monomers for preparation of amide linked RNA: synthesis of C3′-homologated nucleoside amino acids from D-xylose

TETRAHEDRON

卷:66

Article

Tanui, Paul¹  Kullberg, Martin¹  Song, Ni¹  Chivate, Yashodhan¹  Rozners, Eriks¹ 

[1] SUNY Binghamton, Dept Chem, Binghamton, NY 13902 USA

关键词: RNA;    Modified nucleoside;    Amide internucleoside linkage;    Carbohydrate synthesis;    Selective reduction of ester;   

DOI  :  10.1016/j.tet.2010.04.110

来源: Elsevier

【 摘 要 】

Amides as neutral and hydrophobic internucleoside linkages in RNA are highly interesting modifications for RNA interference. However, testing amides in siRNAs is hampered by the shortage of efficient methods to synthesize the monomeric building blocks, the nucleoside amino acid equivalents. This paper reports an efficient synthesis of protected ribonucleoside 5'-amino 3'-carboxylic acids from D-xylose in 14 steps 7% overall yield. The key features that ensure efficiency and ease of operations are chemo-selective reduction of the ester and minimization of protecting group manipulation. (C) 2010 Elsevier Ltd. All rights reserved.

【 授权许可】

Free