CAS: 25796-04-7; 2-Amino-3-(4-Bromo-1H-Indol-3-yl)Propanoic Acid

该化合物是一种试普多芬的溴化蛋白衍生物,在异酚环的4位置上有一个反应性溴代二苯替代物,这种结构改变增强了其在有机合成和制药研究中作为多用途中间体的效用.该化合物独特的溴协会有利于选择性的交叉反应,使得能够建造复杂的以多醇为基础的脚架.它的手腕中心和碳酸功能进一步允许在Peptide化学和生物活性分子设计中应用.由于高纯度和明确界定的再活性,这种化合物对于针对与血清相关的路径或蛋白碱合成的医学化学研究特别有用.建议由于潜在的敏感性,在惰性条件下进行妥善处理.

结构式图片

上下游产品

2-(4-Bromo-1H-indol-3-ylmethyl)-2-formylamino-malonic acid diethyl ester 3-(Dimethylaminomethyl)indole 1-(4-bromo-1H-indol-3-yl)-N,N-dimethylmethanamine 1-(N-triisopropylsilyl-1H-indol-3-yl)-N,N-dimethylmethanamine

合成工艺路线路线简述

  • 合成目标产物 4-Bromo-Dl-Tryptophan 主要起始原料 Gramine
  • (文献来源)合成步骤主要原料 Gramine
📜4-溴芦竹碱置于盐酸,Sodium Hydroxide,溶剂黄146体系中,用 甲苯 用作溶剂,化学反应 96.0H,反应生成2-氨基-3-(4-溴-1H-吲哚-3-基)丙酸
参考文献:对映体合成的(R)-4-氨基-5-氧代-1,3,4,5-四氢苯并[cd]吲哚,一种含有麦角三环核的高级中间体.
标题:对映体合成的(R)-4-氨基-5-氧代-1,3,4,5-四氢苯并[cd]吲哚,一种含有麦角三环核的高级中间体.
摘要:我们报告了(R)-4-氨基-5-氧代-1,3,4,5-四氢苯并[cd]吲哚的对映体特异性合成的新策略.该化合物是高级中间体,其中包含许多四环麦角生物碱的三环核心.我们的方法涉及从吲哚基锂物种与掩蔽的丝氨酸的偶联初始合成d-4-溴色氨酸.α-氨基位置被n-三苯甲基保护,确保在随后的有机金属环化反应中该位置的对映体完整性.通过用boc基团保护吲哚氮或将α-氨基酮还原为相应的β-氨基醇,可实现三环的稳定.
Doi:10.1021/jo981723S

海关参考信息

专利信息


专利号:US-10752927-B2
优先权日:2018-03-01
标 题 :Method for the synthesis of tryptophan analogs in aqueous solvents at reduced temperatures
发明人:BOVILLE CHRISTINA E; ROMNEY DAVID K; ALMHJELL PATRICK J; SIEBEN MICHAELA M
权利人:CALIFORNIA INST OF TECHN
摘要:The present disclosure provides methods for preparing tryptophans and tryptophan derivatives. The methods include: combining i) an indole substrate or azulene substrate, ii) a serine substrate, and iii) an engineered tryptophan synthase β-subunit (TrpB); and maintaining the resulting mixture under conditions sufficient to form the product compound. The engineered TrpB comprises a PLP binding loop mutation, a helix 1 mutation, a strand 7-8 mutation, or a combination thereof. New TrpB variants are also described.

专利号:US-2019271016-A1
优先权日:2018-03-01
标题:Method for the synthesis of tryptophan analogs in aqueous solvents at reduced temperatures

专利号:EP-3759227-A1
优先权日:2018-03-01
标题:Improved method for the synthesis of tryptophan analogs in aqueous solvents at reduced temperatures

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品牌试剂参考报价(招募中)

📌 第三方产品分析报告

✅ COA系统入驻 | 共享模式

主要参考文献

参考标题:Total Synthesis Without Protection: Three-Step Synthesis Of Optically Active Clavicipitic Acids By A Biomimetic Route
作者:Yuusaku Yokoyama,Hidemasa Hikawa,Masaharu Mitsuhashi,Aki Uyama,Yasuhiro Hiroki,Yasuoki Murakami |发布日期:2004.3
摘要:A Three-Step Synthesis Of A Mixture Of Optically Active Cis- And Trans-Clavicipitic Acids 6, Which Are Ergot Alkaloids, Was Achieved, Starting From 4-Bromoindole (7) And Dl-Serine (Dl-2). This Short Synthesis Was Made Possible By Omitting The Protection And Deprotection Steps From The Synthetic Route. The Key Step Was The Spontaneous Cyclization Of 4-Vinyltryptophan (10) Formed From The Heck Reaction

合成参考文献

参考DOI号:10.1021/jo981723s
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