An Environmentally Benign Method for the Synthesis of C-aryl Glycosides
一种环境友好的 C-芳基糖苷合成方法
基本信息
- 批准号:7896053
- 负责人:
- 金额:$ 6.02万
- 依托单位:
- 依托单位国家:美国
- 项目类别:
- 财政年份:2009
- 资助国家:美国
- 起止时间:2009-09-08 至 2011-08-31
- 项目状态:已结题
- 来源:
- 关键词:AcidsAdoptedAntifungal AgentsBenignBiologicalBiological FactorsC-glycosideCarbohydratesCarbonChemical IndustryChemicalsCommunicable DiseasesComplexCorrosivesDevelopmentEcosystemEvaluationFamilyFutureGlycosidesGoalsHealthHumanIsomerismMetalsMethodologyMethodsMindModelingNMR SpectroscopyPharmacologic SubstancePreparationProceduresProcessPropertyProtocols documentationReactionReagentResearchScientistSolventsStagingTemperatureTestingTransition ElementsVariantZincanalogantineoplastic antibioticsaryl halidecatalystfightingimprovedliquid chromatography mass spectrometrynovelprogramsresearch studystereochemistrytooltoxic metal
项目摘要
DESCRIPTION (provided by applicant): The long-term objective of this project is to develop an environmentally friendly method for the preparation of 2-deoxy-C-aryl glycosides, a family of natural products which demonstrate important biological properties such as antitumor, antibiotic and antifungal activities. Previous approaches to the synthesis of this class of compounds have involved the use of corrosive Lewis acids or toxic metals for the preparation of the carbon-carbon linkage between carbohydrate and aromatic moieties. Although we have previously shown that benign organoindium reagents may be employed in fashioning the glycosidic carbon-carbon bond efficiently, we wish to explore a new method that will allow the construction of this bond with the stereochemical configuration found in the natural products. With this goal in mind, we will investigate the preparation and reactivity of benign glycosyl zinc reagents as key intermediates in the synthesis of C-aryl glycosides. It is anticipated that temperature will be a key factor in determining the orientation of the carbon-zinc bond, which ultimately will determine the stereochemistry of the glycosidic carbon-carbon bond. Optimal conditions for the transition-metal catalyzed cross-coupling reaction between the glycosyl zinc reagent and aryl halides or triflates for the formation of the C-glycosides will also be explored. Finally, to assess the broad utility of this method, the preparation of the glycosidic core of the angucycline natural product Sch 47555 will be undertaken, and the mildness of the reaction conditions will be gauged by attempting a late-stage joining of fully functionalized carbohydrate and aromatic units bearing a sensitive O-glycosidic linkage. Because of the pronounced biological activities of the C-aryl glycosides, it is likely that even structural variants and simplified analogs of these natural products will have intriguing properties; as a result, a further aim of our synthetic efforts is to produce sufficient quantities of these substances for pharmacological evaluation. If successful, this research will provide scientists with an additional tool for the assembly of medicinally relevant compounds to fight sickness and infectious disease. Furthermore, if such environmentally benign protocols are widely adopted in the chemical industries, the negative impacts of large-scale chemical processes on fragile ecosystems and the biosphere will be diminished, which in the long term will result in improved human health.
描述(由申请人提供):本项目的长期目标是开发一种制备2-脱氧-C-芳基糖苷的环境友好方法,2-脱氧-C-芳基糖苷是一种天然产物,具有重要的生物学特性,如抗肿瘤、抗生素和抗真菌活性。以前合成这类化合物的方法涉及使用腐蚀性刘易斯酸或有毒金属来制备碳水化合物和芳族部分之间的碳-碳键。虽然我们以前已经表明,良性的有机铟试剂可用于形成有效的糖苷碳-碳键,我们希望探索一种新的方法,将允许这种键的建设与天然产物中发现的立体化学构型。考虑到这一目标,我们将研究良性糖基锌试剂作为C-芳基糖苷合成中的关键中间体的制备和反应性。预计温度将是决定碳-锌键取向的关键因素,其最终将决定糖苷碳-碳键的立体化学。过渡金属催化的交叉偶联反应之间的糖基锌试剂和芳基卤化物或三氟甲磺酸酯的C-糖苷的形成的最佳条件也将进行探索。最后,为了评估该方法的广泛实用性,将进行安卡环素天然产物Sch 47555的糖苷核心的制备,并通过尝试后期加入具有敏感O-糖苷键的完全官能化的碳水化合物和芳族单元来测量反应条件的温和性。由于C-芳基糖苷的显著生物活性,这些天然产物的甚至结构变体和简化的类似物也可能具有有趣的性质;因此,我们合成努力的另一个目的是生产足够量的这些物质用于药理学评价。如果成功,这项研究将为科学家提供一个额外的工具,用于组装与医学相关的化合物来对抗疾病和传染病。此外,如果化学工业广泛采用这种无害环境的议定书,大规模化学工艺对脆弱的生态系统和生物圈的负面影响将减少,从长远来看,这将改善人类健康。
项目成果
期刊论文数量(7)
专著数量(0)
科研奖励数量(0)
会议论文数量(0)
专利数量(0)
Synthesis of alkynyl ethers and low-temperature sigmatropic rearrangement of allyl and benzyl alkynyl ethers.
- DOI:10.1021/ol802147h
- 发表时间:2008-11-06
- 期刊:
- 影响因子:5.2
- 作者:Sosa, Juan R.;Tudjarian, Armen A.;Minehan, Thomas G.
- 通讯作者:Minehan, Thomas G.
Concise total syntheses of aspalathin and nothofagin.
aspalathin 和 nothofagin 的简明全合成。
- DOI:10.1021/ol100315g
- 发表时间:2010
- 期刊:
- 影响因子:5.2
- 作者:Yepremyan,Akop;Salehani,Baback;Minehan,ThomasG
- 通讯作者:Minehan,ThomasG
A sequential indium-mediated aldehyde allylation/palladium-catalyzed cross-coupling reaction in the synthesis of 2-deoxy-beta-C-aryl glycosides.
- DOI:10.1021/ol901353f
- 发表时间:2009-08-20
- 期刊:
- 影响因子:5.2
- 作者:Moral JA;Moon SJ;Rodriguez-Torres S;Minehan TG
- 通讯作者:Minehan TG
An environmentally benign synthesis of cis-2,6-disubstituted tetrahydropyrans via indium-mediated tandem allylation/Prins cyclization reaction.
通过铟介导的串联烯丙基化/Prins环化反应环境友好地合成顺式2,6-二取代四氢吡喃。
- DOI:10.1021/jo7016857
- 发表时间:2008
- 期刊:
- 影响因子:0
- 作者:Pham,Minh;Allatabakhsh,Amir;Minehan,ThomasG
- 通讯作者:Minehan,ThomasG
[3,3]-Sigmatropic rearrangement/5-exo-dig cyclization reactions of benzyl alkynyl ethers: synthesis of substituted 2-indanones and indenes.
苄基炔基醚的[3,3]-Sigmatropic重排/5-exo-dig环化反应:取代的2-茚满酮和茚的合成。
- DOI:10.1021/jo200271s
- 发表时间:2011
- 期刊:
- 影响因子:0
- 作者:Tudjarian,ArmenA;Minehan,ThomasG
- 通讯作者:Minehan,ThomasG
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Thomas Gerard Minehan其他文献
Thomas Gerard Minehan的其他文献
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{{ truncateString('Thomas Gerard Minehan', 18)}}的其他基金
Synthesis and DNA binding affinity evaluation of novel gilvocarcin-C-glucosides
新型吉沃卡星-C-葡萄糖苷的合成及DNA结合亲和力评价
- 批准号:
8473229 - 财政年份:2011
- 资助金额:
$ 6.02万 - 项目类别:
Synthesis and DNA binding affinity evaluation of novel gilvocarcin-C-glucosides
新型吉沃卡星-C-葡萄糖苷的合成及DNA结合亲和力评价
- 批准号:
8078218 - 财政年份:2011
- 资助金额:
$ 6.02万 - 项目类别:
Synthesis and DNA binding affinity evaluation of novel gilvocarcin-C-glucosides
新型吉沃卡星-C-葡萄糖苷的合成及DNA结合亲和力评价
- 批准号:
8264739 - 财政年份:2011
- 资助金额:
$ 6.02万 - 项目类别:
An Environmentally Benign Method for the Synthesis of C-aryl Glycosides
一种环境友好的 C-芳基糖苷合成方法
- 批准号:
7287967 - 财政年份:2007
- 资助金额:
$ 6.02万 - 项目类别:
An Environmentally Benign Method for the Synthesis of C-aryl Glycosides
一种环境友好的 C-芳基糖苷合成方法
- 批准号:
7487529 - 财政年份:2007
- 资助金额:
$ 6.02万 - 项目类别:
An Environmentally Benign Method for the Synthesis of C-aryl Glycosides
一种环境友好的 C-芳基糖苷合成方法
- 批准号:
7678360 - 财政年份:2007
- 资助金额:
$ 6.02万 - 项目类别:
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