由5-氨基-1-β-D-呋喃核糖基-4-咪唑甲酰胺合成鸟苷及其衍生物。IV. 通过氰胺衍生物合成鸟苷的新途径。
Synthesis of guanosine and its derivatives from 5-amino-1-beta-D-ribofuranosyl-e-imidazolecarboxamide. IV. A new route to guanosine via cyanamide derivative.
作者信息
Yamazaki A, Okutsu M, Yamada Y
出版信息
Nucleic Acids Res. 1976 Jan;3(1):251-9. doi: 10.1093/nar/3.1.251.
Abstract
4-Cyanamido-5-imidazolecarboxamide (IV) was prepared by brief treatment of 5-(S-methylisothiocarbamoyl) amino-4-imidazolecarboxamide (V) with alkali. Compound VI was converted in an alkaline solution to either guanine (VII) or isoguanine (VIII), depending on the concentration of alkali. This procedure was applied to the synthesis of 2',3'-0-isopropylideneguanosine (XVI) from the riboside of 5-(N'-benzoyl-S-methylthiocarbamoyl) amino-4-imidazolecarboxamide (IX), PROviding a new route to XVI.
摘要
4-氰胺基-5-咪唑甲酰胺（IV）是通过用碱对5-（S-甲基异硫代氨基甲酰基）氨基-4-咪唑甲酰胺（V）进行短暂处理而制备的。化合物VI在碱性溶液中根据碱的浓度转化为鸟嘌呤（VII）或异鸟嘌呤（VIII）。该方法应用于从5-（N'-苯甲酰基-S-甲基硫代氨基甲酰基）氨基-4-咪唑甲酰胺（IX）的核糖苷合成2'，3'-O-异丙叉基鸟苷（XVI），为合成XVI提供了一条新途径。
相似文献
1
Synthesis of guanosine and its derivatives from 5-amino-1-beta-D-ribofuranosyl-e-imidazolecarboxamide. IV. A new route to guanosine via cyanamide derivative.由5-氨基-1-β-D-呋喃核糖基-4-咪唑甲酰胺合成鸟苷及其衍生物。IV. 通过氰胺衍生物合成鸟苷的新途径。
Nucleic Acids Res. 1976 Jan;3(1):251-9. doi: 10.1093/nar/3.1.251.
2
Synthesis of guanosine and its derivatives from 5-amino-1-beta-D-ribofuranosyl-4-imidazolecarboxamide. III. Formation of a novel cycloimidazole nucleoside and its cleavage reactions.由5-氨基-1-β-D-呋喃核糖基-4-咪唑甲酰胺合成鸟苷及其衍生物。III. 一种新型环咪唑核苷的形成及其裂解反应。
Nucleic Acids Res. 1976 Jan;3(1):237-50. doi: 10.1093/nar/3.1.237.
3
A new synthesis of inosine from 5-amino-1-beta-D-ribofuranosyl-4-imidazole-carboxamide.一种由5-氨基-1-β-D-呋喃核糖基-4-咪唑甲酰胺合成肌苷的新方法。
Nucleic Acids Res. 1976 Jan;3(1):231-5. doi: 10.1093/nar/3.1.231.
4
Imidazo[1,2-a]-s-triazine nucleosides. Synthesis and antiviral activity of the N-bridgehead guanine, guanosine, and guanosine monophosphate analogues of imidazo[1,2-a]-s-triazine.
J Med Chem. 1978 Sep;21(9):883-9. doi: 10.1021/jm00207a009.
5
Efficient methods for the synthesis of [2-15N]guanosine and 2'-deoxy[2-15N]guanosine derivatives.[2-¹⁵N]鸟苷和2'-脱氧[2-¹⁵N]鸟苷衍生物的高效合成方法。
Nucleosides Nucleotides Nucleic Acids. 2001 Jan-Feb;20(1-2):59-75. doi: 10.1081/NCN-100001437.
6
Synthesis of guanosine and its derivatives from 5-amino-1-beta-D-ribofuranosyl-4-imidazolecarboxamide. II. Ring closure with sodium methylxanthate.由5-氨基-1-β-D-呋喃核糖基-4-咪唑甲酰胺合成鸟苷及其衍生物。II. 与甲基黄原酸钠的环合反应
J Org Chem. 1967 Oct;32(10):3032-8. doi: 10.1021/jo01285a021.
7
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.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。
Nucleic Acids Res. 1985 Jul 25;13(14):5341-52. doi: 10.1093/nar/13.14.5341.
8
7-Functionalized 7-deazapurine ribonucleosides related to 2-aminoadenosine, guanosine, and xanthosine: glycosylation of pyrrolo[2,3-d]pyrimidines with 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose.与2-氨基腺苷、鸟苷和黄苷相关的7-官能化7-脱氮嘌呤核糖核苷：吡咯并[2,3-d]嘧啶与1-O-乙酰基-2,3,5-三-O-苯甲酰基-D-呋喃核糖的糖基化反应
J Org Chem. 2006 Jan 6;71(1):81-90. doi: 10.1021/jo0516640.
9
Synthesis of guanosine and its derivatives from 5-amino-1-beta-d-ribofuranoxyl-4-imidazolecarboxamide. I. Ring closure with benzoyl isothiocyanate.由5-氨基-1-β-D-呋喃核糖基-4-咪唑甲酰胺合成鸟苷及其衍生物。I. 与苯甲酰异硫氰酸酯的环合反应
J Org Chem. 1967 Jun;32(6):1825-8. doi: 10.1021/jo01281a027.
10
An efficient method for the synthesis of [2-(15)N]guanosine and 2'-deoxy[2-(15)N]guanosine derivatives.
Nucleic Acids Symp Ser. 1999(42):159-60. doi: 10.1093/nass/42.1.159.
本文引用的文献
1
A new and convenient synthesis of 4-amino-5-imidazolecarboxamide.4-氨基-5-咪唑甲酰胺的一种新型便捷合成方法。
J Biol Chem. 1949 Nov;181(1):89-93.
2
Synthesis of guanosine and its derivatives from 5-amino-1-beta-D-ribofuranosyl-4-imidazolecarboxamide. II. Ring closure with sodium methylxanthate.由5-氨基-1-β-D-呋喃核糖基-4-咪唑甲酰胺合成鸟苷及其衍生物。II. 与甲基黄原酸钠的环合反应
J Org Chem. 1967 Oct;32(10):3032-8. doi: 10.1021/jo01285a021.
3
Synthesis of guanosine and its derivatives from 5-amino-1-beta-d-ribofuranoxyl-4-imidazolecarboxamide. I. Ring closure with benzoyl isothiocyanate.由5-氨基-1-β-D-呋喃核糖基-4-咪唑甲酰胺合成鸟苷及其衍生物。I. 与苯甲酰异硫氰酸酯的环合反应
J Org Chem. 1967 Jun;32(6):1825-8. doi: 10.1021/jo01281a027.
Zotero 插件