通过钠盐糖基化方法对某些3-脱氮鸟嘌呤的7-（β-D-呋喃核糖基）和7-（2-脱氧-β-D-呋喃核糖基）衍生物进行新的合成。

A new synthesis of certain 7-(beta-D-ribofuranosyl) and 7-(2-deoxy-beta-D-ribofuranosyl) derivatives of 3-deazaguanine via the sodium salt glycosylation procedure.

作者信息

Gupta P K, Robins R K, Revankar G R

出版信息

Nucleic Acids Res. 1985 Jul 25;13(14):5341-52. doi: 10.1093/nar/13.14.5341.

DOI:10.1093/nar/13.14.5341

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC321869/

Abstract

A facile synthesis of 7-beta-D-ribofuranosyl-3-deazaguanine (1) and certain 8-substituted derivatives of 1 via the sodium salt glycosylation method has been developed. Glycosylation of the sodium salt of methyl 2-chloro(or methylthio)-4(5)-cyanomethylimidazole-5(4)-carboxylate (5 and 13b) with 2,3,5-tri-O-benzoyl-D-ribofuranosyl bromide (6) gave exclusively methyl 2-chloro(or methylthio)-4-cyanomethyl-1-(2,3, 5-tri-O-benzoyl-beta-D-ribofuranosyl)imidazole-5-carboxylate (7 and 14a), respectively. Ammonolysis of 7 and 14a provided 6-amino-2-chloro(or methylthio)-3-beta-D-ribofuranosylimidazo-[4,5-c]pyridin-4(5H)-one (11 and 17), which on subsequent dehalogenation (or dethiation) gave 1. Similarly, reaction of the sodium salt of 5 and 13b with 1-chloro-2-deoxy-3,5-di-O-p-toluoyl-alpha-D-erythro-pentofuranose (8), and ammonolysis of the glycosylated imidazole precursors (9 and 16) gave 6-amino-2-chloro(or methylthio)-3-(2-deoxy-beta-D-erythro-pentofuranosyl) imidazo[4,5-c]-pyridin-4(5H)-one (10a and 15), respectively. Dehalogenation of 10a or dethiation of 15 gave 2'-deoxy-7-beta-D-ribofuranosyl-3-deazaguanine (10b). This procedure provided a direct method of obtaining 10b without the contaminating 9-glycosyl isomer 4.

摘要

通过钠盐糖基化方法，已开发出一种简便合成7-β-D-呋喃核糖基-3-脱氮鸟嘌呤（1）及其某些1的8-取代衍生物的方法。2-氯（或甲硫基）-4（5）-氰基甲基咪唑-5（4）-羧酸甲酯（5和13b）的钠盐与2,3,5-三-O-苯甲酰基-D-呋喃核糖基溴（6）进行糖基化反应，分别仅得到2-氯（或甲硫基）-4-氰基甲基-1-（2,3,5-三-O-苯甲酰基-β-D-呋喃核糖基）咪唑-5-羧酸甲酯（7和14a）。7和14a进行氨解反应得到6-氨基-2-氯（或甲硫基）-3-β-D-呋喃核糖基咪唑并[4,5-c]吡啶-4（5H）-酮（11和17），随后进行脱卤（或脱硫）反应得到1。同样，5和13b的钠盐与1-氯-2-脱氧-3,5-二-O-对甲苯甲酰基-α-D-赤藓戊呋喃糖（8）反应，糖基化的咪唑前体（9和16）进行氨解反应，分别得到6-氨基-2-氯（或甲硫基）-3-（2-脱氧-β-D-赤藓戊呋喃糖基）咪唑并[4,5-c]吡啶-4（5H）-酮（10a和15）。10a脱卤或15脱硫得到2'-脱氧-7-β-D-呋喃核糖基-3-脱氮鸟嘌呤（10b）。该方法提供了一种直接获得10b的方法，而不会产生污染性的9-糖基异构体4。

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