含2′‐O‐α‐D‐核糖呋喃基腺苷的聚(ADP‐核糖)单体的合成

Q4 Chemistry
Sergey N. Mikhailov, Mikhail S. Drenichev, Vladimir E. Oslovsky, Irina V. Kulikova, Piet Herdewijn
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引用次数: 1

摘要

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。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Synthesis of Poly(ADP-ribose) Monomer Containing 2′-O-α-D-Ribofuranosyl Adenosine

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.

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来源期刊
Current Protocols in Nucleic Acid Chemistry
Current Protocols in Nucleic Acid Chemistry Chemistry-Organic Chemistry
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期刊介绍: Published in association with International Society for Nucleosides, Nucleotides & Nucleic Acids (IS3NA) , Current Protocols in Nucleic Acid Chemistry is equally valuable for biotech, pharmaceutical, and academic labs. It is the resource for designing and running successful research projects in the rapidly growing and changing field of nucleic acid, nucleotide, and nucleoside research.
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