Synthesis of C-Nucleosides Related Oxetanocin

C-核苷相关的奥沙坦星的合成

• 批准号: 63870089
• 负责人: YAMANAKA Hiroshi
• 金额: $ 1.79万
• 依托单位: TOHOKU UNIVERSITY
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Developmental Scientific Research
• 财政年份: 1988
• 资助国家: 日本
• 起止时间: 1988 至 1989
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-63870089/
• 关键词: oxetanocin; antiviral activity; uracil; pyrrolopyrimidine; acyclonucleoside; C-nucleoside; organotin compound; palladium-catalyzed reaction; デアザプリン環; オキセタノシン誘導体の合成; デアザプリンの環合成; ヌクレオシド; 抗ウイルス薬の開発

In order to develop the chemistry of heterocyclic compounds having antiviral activities, synthesis of nucleosides relating to oxetanocin was investigated. 1) Ring-Closure to Pyrrolopyrimidines New methods for the synthesis of pyrrolo[2,3-d]pyrimidine and pyrrolo[3,2- d]pyrimidine derivatives was established as a basic investigation. 2) Synthesis of Uracil-Type C-Nucleoside Starting from 5-bromo-2,4-bis(benzyloxy)pyrimidine, the synthesis of the 5-pyrimidinyloxetanose was accomplished as shown below. 3) Synthesis of Deazapurine-Type Nucleosides On the basis of the results described in Section 1, the following acyclonucleosides was synthesized.

为了发展具有抗病毒活性的杂环化合物的化学，研究了与氧杂环素相关的核苷的合成。1)吡咯并[3，2-d]吡咯并[3，2-d]嘧啶类化合物的合成。2)尿嘧啶C-核苷的合成以5-溴-2，4-二(苄氧基)嘧啶为原料，合成了5-嘧啶氧杂环己糖。3)去氮型核苷的合成在第一节所述结果的基础上，合成了以下非环核苷。

项目成果

Yoshinori Kondo: "Studies on Pyrimidine Derivatives.XLI.Palladium-Catalyzed Cross-Coupling Reaction of Halopyrimidines with Aryl-and Vinyltributylstannanes" Chemical & Pharmaceutical Bulletin. 37. 2814-2816 (1989)

Yoshinori Kondo：“嘧啶衍生物的研究。XLI.钯催化卤代嘧啶与芳基和乙烯基三丁基锡烷的交叉偶联反应”化学

Yuh-ichiro Ichikawa, Setsuko Niitsuma, Kuniki Kato, and Tomohisa Takita: "Preparation of trans-3-(Hydroxymethyl)-2-vinyloxetanocin via Allyloxycarbanion-mediated Carbon-Carbon Bond Formation in Allyl Glycidyl Ether" Journal of Chemical Society, Chemical C

Yuh-ichiro Ichikawa、Setsuko Niitsuma、Kuniki Kato 和 Tomohisa Takita：“通过烯丙氧基碳负离子介导的烯丙基缩水甘油醚中的碳-碳键形成制备反式 3-(羟甲基)-2-乙烯基氧杂环己烷”化学会杂志，化学 C

Yuh-ichiro Ichikawa: "Preparation of trans-3-(Hydroxymethyl)-2-vinyloxetane via Allyoxycarbanion-mediated Carbon-Carbon Bond Formation in Allyl Glycidyl Ether" Journal of Chemical Society,Chemical Communication. 625-626 (1988)

Yuh-ichiro Ichikawa：“通过烯丙基缩水甘油醚中烯丙氧基碳负离子介导的碳-碳键形成制备反式-3-（羟甲基）-2-乙烯基氧杂环丁烷”《化学学会杂志》，《化学通讯》。

Yoshinori Kondo: "Condensed Heteroaromatic Ring Systems.XVI.Synthesis of Pyrrolo[2,3-d]pyrimidine Derivatives" Chemical & Pharmaceutical Bulletin. 37. 2933-2936 (1989)

近藤义典：“稠合杂芳环系统.XVI.吡咯并[2,3-d]嘧啶衍生物的合成”化学

Yoshinori Kondo, Ryo Watanabe, Takao Sakamoto, and Hiroshi Yamanaka: "Condensed Heteroaromatic Ring Systems. XVI. Synthesis of Pyrrolo[2,3-d]pyrimidine Derivatives" Chemical & Pharmaceutical Bulletin. 37. 2933-2936 (1989)

Yoshinori Kondo、Ryo Watanabe、Takao Sakamoto 和 Hiroshi Yamanaka：“稠合杂芳环系统。XVI. 吡咯并[2,3-d]嘧啶衍生物的合成”化学