Sergey N. Mikhailov, Mikhail S. Drenichev, Vladimir E. Oslovsky, Irina V. Kulikova, Piet Herdewijn
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Abstract
In this article, the earlier reported procedure for the synthesis of 2′-O -β-D -ribofuranosyl nucleosides was extended to the synthesis of 2′-O -α-D -ribofuranosyl adenosine, a monomeric unit of poly(ADP-ribose). It consists in condensation of a small excess of 1-O -acetyl-2,3,5-tri-O -benzoyl-α,β-D -arabinofuranose activated with tin tetrachloride with 3′,5′-O -tetra-isopropyldisiloxane-1,3-diyl-ribonucleosides in 1,2-dichloroethane. The following debenzoylation and silylation of arabinofuranosyl residue and inversion of configuration at C-2ʹʹ atom of arabinofuranosyl residue and final removal of silyl protective groups gave 2′-O -α-D -ribofuranosyl adenosine in overall 13% to 21% yield. © 2019 by John Wiley & Sons, Inc.
含2′‐O‐α‐D‐核糖呋喃基腺苷的聚(ADP‐核糖)单体的合成
在这篇文章中,先前报道的合成2′‐O‐β‐D‐核糖呋喃烷核苷的方法被扩展到合成2′‐O‐α‐D‐核糖呋喃烷腺苷,这是一种聚(ADP‐核糖)的单体单位。它由少量过量的1 - O -乙酰- 2,3,5 -三- O -苯甲酰- α,β - D -阿拉伯铀糖与3 ',5 ' - O -四异丙基二硅氧烷- 1,3 -二基核糖核苷在1,2 -二氯乙烷中缩合而成。接下来对阿拉伯糖糠基残基进行去苯甲酰化和硅基化,并在阿拉伯糖糠基残基的C - 2 - 2原子上进行构型反转,最后去除硅基保护基团,得到2′- O - α - D -核糠基腺苷,总收率为13%至21%。©2019 by John Wiley & Sons, Inc。
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