Production of novel isoquinoline-containing functional reagents and new developmet

新型含异喹啉功能试剂的生产及新进展

基本信息

  • 批准号:
    15590019
  • 负责人:
  • 金额:
    $ 2.24万
  • 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
  • 起止时间:
    2003 至 2005
  • 项目状态:
    已结题

项目摘要

We reported a novel and chemoselective tert-butoxycarbonylation reagent, 1-tert-butoxy-2-tert-butoxycarbonyl-1, 2-dihydroisoquinoline (BBDI), which was easily prepared in quantitative yield by the reaction of isoquinoline with Boc_2O. BBDI effected easily the tert-butoxycarbonylation for acidic substrates in the absence of bases rather than basic ones, while that for acidic compounds such as phenols, carboxylic acids using Boc_2O required some base. The synthesis of carboxylic esters is one of the most fundamental and pivotal protocols for producing natural and synthetically useful compounds in organic chemistry. The coupling reactions between activated derivatives of carboxylic acids and alcohols have been employed. These procedures are of considerable interest, especially as relate to the manipulation of peptides or complicated biologically active compounds such as macrolides. A simple and mild esterification of N-protected amino acids using BBDI as a novel condensing reagent in a on … More e-pot method was developed. This protocol has several advantages including the use of nearly equimolar amounts of alcohols, no requirement for additives, and no racemization occurs. Next, we developed a novel BBDI-catalyzed esterification of N-protected amino acids in the presence of Boc_2O under simple and mild conditions. Although a variety of methods for acid-catalyzed esterification reactions have been reported, the use of a nearly neutral catalyst such as BBDI has not been extensively investigated. Further, it was found that catalytic esterification using BBDI typed reagent derived from electron-rich isoquinoline such as 6-methoxyisoquinoline shortened a reaction time. The synthesis of carboxylic amide is one of the most fundamental and pivotal protocols for producing natural and synthetically useful compounds such as peptides in organic chemistry. We succeeded a simple and mild amidation that uses nearly equimolar amounts of a variety of carboxylic acids and amines and BBDI without the need for any additives. Less
本文报道了一种新型的化学选择性叔丁氧基羰基化试剂,1-叔丁氧基-2-叔丁氧基羰基- 1,2 -二氢异喹啉(BBDI),该试剂由异喹啉与Boc_2O反应制备而得。BBDI对酸性底物在无碱条件下的叔丁基羰基化反应较碱性底物容易,而用Boc_2O对酚类、羧酸等酸性化合物的叔丁基化反应则需要一定的碱。羧酸酯的合成是有机化学中生产天然和合成有用化合物的最基本和关键的方法之一。研究了羧酸和醇的活性衍生物之间的偶联反应。这些程序是相当有趣的,特别是涉及到多肽或复杂的生物活性化合物,如大环内酯的操作。以BBDI为缩合试剂,在电子锅中进行了简单温和的n保护氨基酸酯化反应。该方案有几个优点,包括使用几乎等摩尔量的醇,不需要添加剂,不发生外消旋作用。接下来,我们在简单温和的条件下,在Boc_2O存在下,开发了一种新的bbdi催化n保护氨基酸的酯化反应。虽然已经报道了多种酸催化酯化反应的方法,但使用BBDI等近中性催化剂尚未进行广泛的研究。进一步研究发现,用6-甲氧基异喹啉等富电子异喹啉衍生的BBDI型试剂催化酯化可缩短反应时间。羧酸酰胺的合成是有机化学中生产天然和合成有用化合物如肽的最基本和关键的方法之一。我们成功地获得了一种简单而温和的酰胺,它使用了几乎等量的各种羧酸、胺和BBDI,而不需要任何添加剂。少

项目成果

期刊论文数量(14)
专著数量(0)
科研奖励数量(0)
会议论文数量(0)
专利数量(0)
公開特許公報(A)
已发表的专利出版物(A)
  • DOI:
  • 发表时间:
    2004
  • 期刊:
  • 影响因子:
    0
  • 作者:
  • 通讯作者:
A novel 1-tert-butoxy-2-tert-butoxycarbonyl-1,2-dihydroisoquinoline (BBDI)-catalyed esterification of N-protected amino acids with nearly equimolar amounts of alcohols in the presence of Boc_2O
在 Boc_2O 存在下,一种新型 1-叔丁氧基-2-叔丁氧基羰基-1,2-二氢异喹啉 (BBDI) 催化的 N-保护氨基酸与近等摩尔量的醇的酯化反应
  • DOI:
  • 发表时间:
    2006
  • 期刊:
  • 影响因子:
    0
  • 作者:
    Saito;Y.;Watanabe;T.;Takahata;H.
  • 通讯作者:
    H.
Simple and mild esterification of N-protected amino acids with nearly equimolar amounts of aldohols usig 1-tert-butoxy-2-tert-butoxycarbonyl-1,2-dihydroisoquinoline
使用 1-叔丁氧基-2-叔丁氧基羰基-1,2-二氢异喹啉对 N-保护氨基酸与近等摩尔量的醇进行简单温和的酯化
  • DOI:
  • 发表时间:
    2005
  • 期刊:
  • 影响因子:
    0
  • 作者:
    Saito;Y.;Yamaki;T;Kohashi;F.;Watanabe;T.;Ouchi;H.;Takahata;H.
  • 通讯作者:
    H.
A novel 1-tert-butoxy-2-tert-butoxycarbonyl-1,2dihydroisoquinoline (BBDI)-catalyzed esterification of N-protected amino acids with nearly equimolar amounts of alcohols in the presence of BoC2O
  • DOI:
    10.1016/j.tetlet.2006.02.149
  • 发表时间:
    2006-05-01
  • 期刊:
  • 影响因子:
    1.8
  • 作者:
    Saito, Y;Watanabe, T;Takahata, H
  • 通讯作者:
    Takahata, H
Simple and mild esterification of N-protected amino acids with nealy equimolar amounts of alcohols using 1-tert-butoxy-2-tert-butoxycarbonyl-1,2-dihydroisoquinoline
使用 1-叔丁氧基-2-叔丁氧基羰基-1,2-二氢异喹啉对 N-保护氨基酸与近等摩尔量的醇进行简单温和的酯化
  • DOI:
  • 发表时间:
    2005
  • 期刊:
  • 影响因子:
    0
  • 作者:
    Saito;Y.;Yamaki;T.;Kohashi;F.;Watanabe;T.;Ouchi;H;Takahata;H.
  • 通讯作者:
    H.
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TAKAHATA Hiroki其他文献

TAKAHATA Hiroki的其他文献

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{{ truncateString('TAKAHATA Hiroki', 18)}}的其他基金

Medicinal scientific study based on imiosugar C-glycosides mimics
基于亚咪糖C-糖苷模拟物的药用科学研究
  • 批准号:
    22590104
  • 财政年份:
    2010
  • 资助金额:
    $ 2.24万
  • 项目类别:
    Grant-in-Aid for Scientific Research (C)
Synthesis of Carbohydrate-like Alkaloids using Catalytic Asymmetric Reaction
催化不对称反应合成碳水化合物类生物碱
  • 批准号:
    18590012
  • 财政年份:
    2006
  • 资助金额:
    $ 2.24万
  • 项目类别:
    Grant-in-Aid for Scientific Research (C)
Synthesis of C_2- symmetric α, α'-disubstituted azacycloalkanes as chiral building blocks and their application
C_2-对称α,α-二取代氮杂环烷烃手性结构单元的合成及其应用
  • 批准号:
    12672050
  • 财政年份:
    2000
  • 资助金额:
    $ 2.24万
  • 项目类别:
    Grant-in-Aid for Scientific Research (C)
Creation of C2-Symmetric Molecules using An Asymmetric Dihydroxylation and Its Application
不对称二羟基化制备C2对称分子及其应用
  • 批准号:
    07672260
  • 财政年份:
    1995
  • 资助金额:
    $ 2.24万
  • 项目类别:
    Grant-in-Aid for Scientific Research (C)
Origination of functional chiral building blocks using asymmetric acylation and application to the synthesis of biologically active compounds
利用不对称酰化衍生功能性手性构件及其在生物活性化合物合成中的应用
  • 批准号:
    05671743
  • 财政年份:
    1993
  • 资助金额:
    $ 2.24万
  • 项目类别:
    Grant-in-Aid for General Scientific Research (C)
A Synthetic Study of Biologically Active Compounds using Intramolecular Amidation
利用分子内酰胺化合成生物活性化合物的研究
  • 批准号:
    63570986
  • 财政年份:
    1988
  • 资助金额:
    $ 2.24万
  • 项目类别:
    Grant-in-Aid for General Scientific Research (C)

相似海外基金

AP2/ERF transcription factors involved in the regulation of isoquinoline alkaloid biosynthesis
AP2/ERF转录因子参与异喹啉生物碱生物合成的调节
  • 批准号:
    18K14439
  • 财政年份:
    2018
  • 资助金额:
    $ 2.24万
  • 项目类别:
    Grant-in-Aid for Early-Career Scientists
Exploration of Fluorescent Ligands based on Quinoline and Isoquinoline
基于喹啉和异喹啉的荧光配体的探索
  • 批准号:
    15K05454
  • 财政年份:
    2015
  • 资助金额:
    $ 2.24万
  • 项目类别:
    Grant-in-Aid for Scientific Research (C)
Preparaion of Novel Anticancer Agents based on Isoquinoline Marine Natural Products
基于异喹啉海洋天然产物的新型抗癌药物的制备
  • 批准号:
    15K07873
  • 财政年份:
    2015
  • 资助金额:
    $ 2.24万
  • 项目类别:
    Grant-in-Aid for Scientific Research (C)
グアニン四重鎖形成制御を介したフラボノイドの生理活性発現機序の解明
通过鸟嘌呤四链体形成调控阐明黄酮类化合物的生理活性表达机制
  • 批准号:
    26750366
  • 财政年份:
    2014
  • 资助金额:
    $ 2.24万
  • 项目类别:
    Grant-in-Aid for Young Scientists (B)
Characterization of molecular evolution of plant isoquinoline alkaloid biosynthesis and its application to metabolic engineering
植物异喹啉生物碱生物合成分子进化表征及其在代谢工程中的应用
  • 批准号:
    26221201
  • 财政年份:
    2014
  • 资助金额:
    $ 2.24万
  • 项目类别:
    Grant-in-Aid for Scientific Research (S)
Development for medicinal chemistry on antitumor isoquinoline marine natural products as lead compound
以海洋天然产物异喹啉为先导化合物的药物化学研究进展
  • 批准号:
    23590019
  • 财政年份:
    2011
  • 资助金额:
    $ 2.24万
  • 项目类别:
    Grant-in-Aid for Scientific Research (C)
Therapeutic effects of isoquinoline alkaloids isolated from Coptis Rhizoma, potential anti-glomerulonephritis
黄连异喹啉生物碱的治疗作用,潜在的抗肾小球肾炎作用
  • 批准号:
    23790966
  • 财政年份:
    2011
  • 资助金额:
    $ 2.24万
  • 项目类别:
    Grant-in-Aid for Young Scientists (B)
Synthetic Biology Pathways to Isoquinoline Alkaloids
异喹啉生物碱的合成生物学途径
  • 批准号:
    BB/G014426/1
  • 财政年份:
    2009
  • 资助金额:
    $ 2.24万
  • 项目类别:
    Research Grant
Molecular characterization of isoquinoline alkaloid biosynthesis and its reconstitution in plant and microbial cells
异喹啉生物碱生物合成的分子特征及其在植物和微生物细胞中的重建
  • 批准号:
    21248013
  • 财政年份:
    2009
  • 资助金额:
    $ 2.24万
  • 项目类别:
    Grant-in-Aid for Scientific Research (A)
Biosynthetic engineering of isoquinoline alkaloids in microbes
微生物中异喹啉生物碱的生物合成工程
  • 批准号:
    20200036
  • 财政年份:
    2008
  • 资助金额:
    $ 2.24万
  • 项目类别:
    Grant-in-Aid for Scientific Research on Innovative Areas (Research a proposed research project)
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