碘代三甲基硅烷在核苷化过程中的应用。

The use of iodotrimethylsilane in nucleosidation procedure.

作者信息

Tocik Z, Earl R A, Beránek J

出版信息

Nucleic Acids Res. 1980 Oct 24;8(20):4755-61. doi: 10.1093/nar/8.20.4755.

DOI:10.1093/nar/8.20.4755

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC324385/

Abstract

1-O-Acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (I) was reacted with iodotrimethylsilane (II) and the product, the glycosyl iodide, was coupled with silylated uracil to afford 1-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)uracil (III; 89%), with silyated cytosine to afford, on subsequent acetylation, 1-(2,3,5-tri-O-benzoyl-beta-0D-ribofuranosyl)-4-acetamido-2-(1H)-pyrimidinone (IVb; 81%), and with chloromercuri-N-benzoyl-adenine to afford Va and on subsequent debenzoylation, adenosine (Vb; 49%).

摘要

1 - O - 乙酰基 - 2,3,5 - 三 - O - 苯甲酰基 - β - D - 呋喃核糖（I）与碘代三甲基硅烷（II）反应，所得产物糖基碘与硅烷化的尿嘧啶偶联，得到1 - （2,3,5 - 三 - O - 苯甲酰基 - β - D - 呋喃核糖基）尿嘧啶（III；产率89%）；与硅烷化的胞嘧啶偶联，随后乙酰化得到1 - （2,3,5 - 三 - O - 苯甲酰基 - β - D - 呋喃核糖基） - 4 - 乙酰氨基 - 2 - （1H） - 嘧啶酮（IVb；产率81%）；与氯汞基 - N - 苯甲酰基腺嘌呤反应得到Va，随后脱苯甲酰基得到腺苷（Vb；产率49%）。

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本文引用的文献

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Proc Natl Acad Sci U S A. 1978 Jan;75(1):4-6. doi: 10.1073/pnas.75.1.4.

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The glycosyl halides and their derivatives.卤代糖及其衍生物。

Adv Carbohydr Chem. 1955;10:207-56. doi: 10.1016/s0096-5332(08)60393-8.

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