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Updated: Jul 28, 2025

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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
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建立一个一二硫化物驱动的循环合成与3-Nitro-2-pyridinesulfenate
Hayate Shida1, Akihiro Taguchi1, Sho Konno1
1Department of Medicinal Chemistry, School of Pharmacy, Tokyo University of Pharmacy and Life Sciences.
Chemical & pharmaceutical bulletin
|May 31, 2023
概括
我们开发了一种用于循环二硫化的新型单固相合成方法. 这种方法简化了净化,并产生高纯度的,通过催产素合成证明了这一点.
科学领域:
- 有机化学 有机化学
- 类化学 类化学
- 生物化学 生物化学
背景情况:
- 循环二硫化是具有治疗潜力的重要生物分子.
- 传统的合成方法通常涉及复杂的净化步骤.
- 这些的高效和可扩展的合成仍然是一个挑战.
研究的目的:
- 为了开发一个精简的,单一合成周期性二硫化.
- 为了提高合成的循环的纯度和产量.
- 通过催产素合成来证明该方法的适用性.
主要方法:
- 固相合成方法. 固相合成方法.
- 以二硫化物驱动的循环化策略.
- 利用硫化和Ag+促进的酸方法进行结合和循环.
主要成果:
- 实现了循环二硫化的单合成.
- 在13个步骤中成功合成了催产素,具有28%的隔离产量.
- 消除了复杂的加工程序,使得高纯度产品的分离成为可能.
结论:
- 开发的单固体相方法对于合成循环二硫化来说是有效的.
- 这种方法简化了净化,提高了产品的纯度.
- 该方法对可扩展的循环的生产具有前景.
相关概念视频
Preparation and Reactions of Sulfides
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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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Preparation of Nitriles
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One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
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