methyl (2R,3S)-3-bromo-2-((tert-butoxycarbonyl)amino)butanoate | 1054609-06-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2R,3S)-3-bromo-2-((tert-butoxycarbonyl)amino)butanoate
• 英文别名: methyl (2R,3S)-3-bromo-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate
• CAS: 1054609-06-1
• 化学式: C₁₀H₁₈BrNO₄
• 分子量: 296.161
• InChiKey: FBGHOPPMAMIKCL-BQBZGAKWSA-N

物化性质

• 沸点：
  332.0±32.0 °C(Predicted)
• 密度：
  1.325±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.84
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl (2R,3S)-3-bromo-2-((tert-butoxycarbonyl)amino)butanoate 在 盐酸 作用下， 以 1,4-二氧六环 、 甲醇 、 乙腈 为溶剂， 反应 15.0h， 生成 methyl (2R,3R)-2-amino-3-((trifluoromethyl)selanyl)butanoate hydrochloride
  参考文献：
  名称：

  CF3Se取代的α-氨基酸衍生物的合成及生物学评价

  摘要：

  将'Se'置于选择性： CF 3 Se 含α-氨基酸衍生物很容易由天然氨基酸和[Me 4 N][SeCF 3 ]合成。一些衍生物被发现是 MCF-7、HCT116 和 SK-OV-3 细胞的有效抑制剂。这些结果暗示CF 3 Se 部分可用作生物活性分子的合成和修饰中的潜在药学相关基团。

  DOI：

  10.1002/cmdc.202100451
• 作为产物：
  描述：

  N-[(1,1-dimethylethoxy)carbonyl]-O-[(4-methylphenyl)sulfonyl]-L-threonine methyl ester 在 magnesium bromide ethyl etherate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 以9 %的产率得到methyl (2R,3S)-3-bromo-2-((tert-butoxycarbonyl)amino)butanoate
  参考文献：
  名称：

  Divergent reactivities of 2-pyridyl sulfonate esters. Exceptionally mild access to alkyl bromides and 2-substituted pyridines

  摘要：

  A series of 2- and 3-pyridyl sulfonate and tosylate esters of primary and secondary alcohols were synthesized and evaluated in the bromination reaction with MgBr2·Et2O. The greater coordinating ability of the 2-pyridyl sulfonate esters accounted for its observed superior reactivity and selectivity. Reaction of neopentyl and phenyl 2-pyridyl sulfonates with a variety of aryl and heteroaryl Li reagents led to 2-substituted pyridines at temperatures as low as −78 °C via an SNAr process. Mechanistic considerations are discussed.

  DOI：

  10.1139/cjc-2020-0510

文献信息

• Synthesis of Enantiopure Unnatural Amino Acids by Metallaphotoredox Catalysis
  作者：Tomer M. Faraggi、Caroline Rouget-Virbel、Juan A. Rincón、Mario Barberis、Carlos Mateos、Susana García-Cerrada、Javier Agejas、Oscar de Frutos、David W. C. MacMillan

  DOI：10.1021/acs.oprd.1c00208

  日期：2021.8.20

  wide array of optically pure unnatural amino acids. This method utilizes a photocatalytic cross-electrophile coupling between a bromoalkyl intermediate and a diverse set of aryl halides to produce artificial analogues of phenylalanine, tryptophan, and histidine. The reaction is tolerant of a broad range of functionalities and can be leveraged toward the scalable synthesis of valuable pharmaceutical scaffolds

  我们在本文中描述了将丝氨酸转化为多种光学纯非天然氨基酸的两步过程。该方法利用溴代烷基中间体和多种芳基卤化物之间的光催化交叉亲电偶联来生产苯丙氨酸、色氨酸和组氨酸的人工类似物。该反应具有广泛的功能，可用于通过流动技术可扩展地合成有价值的药物支架。
• Oxidative Deselenization of Selenocysteine: Applications for Programmed Ligation at Serine
  作者：Lara R. Malins、Nicholas J. Mitchell、Sheena McGowan、Richard J. Payne

  DOI：10.1002/anie.201504639

  日期：2015.10.19

  Despite the unique chemical properties of selenocysteine (Sec), ligation at Sec is an under‐utilized methodology for protein synthesis. We describe herein an unprecedented protocol for the conversion of Sec to serine (Ser) in a single, high‐yielding step. When coupled with ligation at Sec, this transformation provides a new approach to programmed ligations at Ser residues. This new reaction is compatible

  尽管硒代半胱氨酸（Sec）具有独特的化学性质，但在Sec上进行连接仍是蛋白质合成中未得到充分利用的方法。我们在这里描述了一个前所未有的协议，可以在一个高收益的步骤中将Sec转换为丝氨酸（Ser）。当与Sec处的连接结合时，这种转化为Ser残基处的程序化连接提供了一种新方法。该新反应与多种功能兼容，包括存在未保护的氨基酸侧链和附加的聚糖。快速合成上皮糖蛋白MUC5AC和MUC4的复杂糖肽片段以及结构化的不含半胱氨酸（Cys）的蛋白eglin C的快速合成证明了该方法的实用性。
• Simple and efficient synthesis of allo- and threo-3,3′-dimethylcystine derivatives in enantiomerically pure form
  作者：R.B. Nasir Baig、V. Sai Sudhir、Srinivasan Chandrasekaran

  DOI：10.1016/j.tetasy.2008.06.001

  日期：2008.6

  A simple and efficient method for the synthesis of allo- and threo-3,3'-dimethylcystine derivatives is reported. Various tosyl and bromo derivatives of Cbz-, Boc-, and Fmoc- Protected threonine rnethyl esters have been prepared and subjected to nucleophilic substitution with potassium thiocyanate in acetonitrile to yield the corresponding thiocyanate derivatives in moderate yield. The thiocyanates are readily converted to the corresponding allo- and threo-3,3'-dimethylcystine derivatives via reductive dimerization with benzyltriethylammonium tetrathiomolybdate. (C) 2008 Elsevier Ltd. All rights reserved.