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Synthetk Studies on Multi Sorts of Biologically Active Cormpounds Using Nitrones Related to Amino Acids and Sugars

Synthetk Studies on Multi Sorts of Biologically Active Cormpounds Using Nitrones Related to Amino Acids and Sugars
氨基酸和糖相关硝酮合成多种生物活性化合物的研究
批准号:
15590003
负责人:
TAMURA Osamu
金额:
$2.3万
依托单位:
依托单位国家:
日本
项目类别:
Grant-in-Aid for Scientific Research (C)
财政年份:
2003
资助国家:
日本
项目状态:
已结题
起止时间:
2003 至 2004

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中文摘要
翻译
(1)一种合成方法,即循环氮素从Herniacetals中使用多氧功能,而Sugar则被解释。因此,硝酸盐是由TBAT介导的去氧环化的ω-中氧-O-叔丁基二苯甲基硅氧基配制的,已经由糖衍生物用O-叔丁基二苯甲基羟基胺和中氯酰氯进行了定量治疗。作为本方法的应用,认为可待因、半胱氨酸A_1和半胱氨酸A_2的真实性综合体从环硝基中获得,而从受保护的L-xylose中获得。(2)一种从(S)-苯基糖醇反应,在MgBr_2OEt_2的存在中产生环氮素,以立体电方式给予环氧化物。这种反应被应用于莫纳汀(一种自然的甜味剂)和利可非酸的合成。与乙酰酒精的cycloaddition相比,环氮素与a替代丙烯酸的反应在MgBr_2和Oet_2获得了cycloadducts的存在 ... More posite C4-stcreochemistries.这种反应被用于4-epi-monatin合成物。(3)(-)-funebrine和(-)-funebral已完成的第一个合成。该综合体是由甲基糖基化氧化物、用(E)-氯丁胺醇和内分子环氧化物转化的硝酸盐组成的特征序列形成的。主要的环囊已经被充分提炼为氨基乳糖,是(-)-funebrine和(-)-funebral的关键合成中间体。(4)合成(3'R,5'S)-3'-羟基环素,尼古丁的主要代谢物,C-(3-吡咯烷基)氮环加成(2 R)-和(2S)-N-(丙烯酰)硼-10,2-硫酸钠{(2 R)-和(2S)-硫酸钠]被测试。在他们中间,L-胆固醇衍生出的硝酸盐含有立体声环氧化物,与(2S)-硫酸盐作用于环氧化物,它被提炼为(3'R,5'S)-3'-羟基维生素。(5)饮食-老年反应和环氧化在氮素中的应用,代表性的周期循环反应到异环化合物合成的合成已经被审查。Less(低)
英文摘要
(1)A method for the synthesis cyclic nitrones having multi-oxygen functionalities from herniacetals such as sugars was explored. Thus, the nitrones were prepared by TBAT-mediated desilylative cyclization of ω-mesyloxy-O-tert-butyldiphenylsilyloximes, readily prepared from sugar derivatives by a consecutive treatment with O-tert-butyldiphenylsilylhydroxylamine and with mesyl chloride. As an application of this method, concise synthes of codonopsine, hyacinthacine A_1, and hyacinthacine A_2 were reality accomplished from the cyclic nitrone, which was obtained from protected L-xylose.(2)A cyclic nitrone derived from (S)-phenylglycinol reacted with allyl alcohols in the presence of MgBr_2OEt_2 to give cycloadducts stereoselectively. The reaction was applied to syntheses of monatin (a natural sweetener) and lycoperdic acid. In contrast to cycloaddition with allyl alcohols, reactions of the cyclic nitrone with a-substituted acrylates in the absence of MgBr_2・OEt_2 gave cycloadducts having op … More posite C4-stcreochemistries. The reaction was used for the synthesis of 4-epi-monatin.(3)The first syntheses of (-)-funebrine and (-)-funebral were achieved. The syntheses feature sequential formation of the nitrone from methyl glyoxylate with a gulose-derived oxime, transesterification with (E)-crotyl alcohol, and intramolecular cycloaddition. The major cycloadduct was readily elaborated to amino lactone, the key synthetic intermediate of (-)-funebrine and (-)-funebral.(4)To synthesize (3'R,5'S)-3'-hydroxycotinine, the main metabolite of nicotine, cycloaddition of C-(3-pyridyl)nitrones with (2R)-and (2S)-N-(acryloyl)bornane-10,2-sultam {(2R)-and (2S)-sultam] was examined. Among them, L-gulose-derived nitrone underwent stereoselective cycloaddition with (2S)-sultam to afford the cycloadduct, which was elaborated to (3'R,5'S)-3'-hydroxyeotinine.(5)Applications of Diets-Alder reactions and cycloaddition of nitrones, representative peri-cyclic reactions to synthesis of heterocyclic compounds were reviewed. Less
期刊论文(34)
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会议论文
DOI: --
发表时间: 2003
期刊: Synlett
影响因子: 2
作者: [Atsushi Toyao, Osamu Tamura, Hiroko Takagi, Hiroyuki Ishibashi]
通讯作者: Hiroyuki Ishibashi
Highly Stereoselective Synthesis of (-)-Monatin, A High-Intensity Sweetener Using Chelation-Controlled Nitron-Cycloaddition
使用螯合控制硝基环加成高度立体选择性合成高强度甜味剂 (-)-莫纳甜
DOI: --
发表时间: 2003
期刊: Chem.Commun.
影响因子: --
作者: [Osamu Tamura, Tomoya Shiro, Atsushi Toyao, Hiroyuki Ishibashi]
通讯作者: Hiroyuki Ishibashi
Stereoselective Syntheses of 4-Hydroxy-4-substituted Glutamic Acids
4-羟基-4-取代谷氨酸的立体选择性合成
DOI: --
发表时间: 2005
期刊: The Journal of Organic Chemistry 70・12
影响因子: --
作者: [Osamu Tamura, Tomoya Shiro, Mizuho Ogasawara, Atsushi Toyao, Hiroyuki Ishibashi]
通讯作者: Hiroyuki Ishibashi
Stereoselective Syntheses of 4-Hydroxy-4-suhstiitrtrd Gltitarnic Acids
4-羟基-4-亚磺基谷氨酸的立体选择性合成
DOI: --
发表时间:
期刊: J.Org.Chem. (in press)
影响因子: --
作者: [Osamu Tamura, Tornoya Shiro, Mizuho Ogasawara, Atsushi Toyao, Hiroyuki Ishibashi]
通讯作者: Hiroyuki Ishibashi
14
    Development of reactions by means of novel activation of oximes
    • 批准号:
      17K08221
    • 项目类别:
      Grant-in-Aid for Scientific Research (C)
    • 资助金额:
      $2.83万
    • 财政年份:
      2017
    • 负责人:
      TAMURA Osamu
    • 依托单位:
    DEVELOPMENT OF NOVEL NITROGEN-CONTAINING 1,3-DIPOLARS
    • 批准号:
      22590017
    • 项目类别:
      Grant-in-Aid for Scientific Research (C)
    • 资助金额:
      $2.75万
    • 财政年份:
      2010
    • 负责人:
      TAMURA Osamu
    • 依托单位:
    CONSTRUCTION OF POLYCYCLIC SYSTEMS USING OXIDATION OF AROMATIC COMPOUNDS
    • 批准号:
      19590013
    • 项目类别:
      Grant-in-Aid for Scientific Research (C)
    • 资助金额:
      $2.75万
    • 财政年份:
      2007
    • 负责人:
      TAMURA Osamu
    • 依托单位:
    Documentary Studies on the French Constitution of 1795.
    • 批准号:
      18530026
    • 项目类别:
      Grant-in-Aid for Scientific Research (C)
    • 资助金额:
      $2.64万
    • 财政年份:
      2006
    • 负责人:
      TAMURA Osamu
    • 依托单位:
    海外基金