methyl (S)-4-((tert-butoxycarbonyl)amino)-3-oxopentanoate | 101669-78-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: methyl (S)-4-((tert-butoxycarbonyl)amino)-3-oxopentanoate
• 英文别名: methyl (4S)-4-{[(tert-butoxy)carbonyl]amino}-3-oxopentanoate；methyl (4S)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopentanoate
• CAS: 101669-78-7
• 化学式: C₁₁H₁₉NO₅
• 分子量: 245.276
• InChiKey: HMITWDFQTIEUAV-ZETCQYMHSA-N

物化性质

• 熔点：
  45-48°C
• 沸点：
  334.7±22.0 °C(Predicted)
• 密度：
  1.097±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (S)-4-((tert-butoxycarbonyl)amino)-3-oxopentanoate 在 3 A molecular sieve 乙酸铵 、 sodium hydroxide 、 sodium cyanoborohydride 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 水 为溶剂， 反应 150.0h， 生成 methyl (3R,5R,6S)-3,6-bis(tert-butoxycarbonylamino)-5-hydroxyheptanoate
  参考文献：
  名称：

  Hashiguchi, Shohei; Kawada, Akira; Natsugari, Hideaki, Journal of the Chemical Society. Perkin transactions I, 1991, # 10, p. 2435 - 2444

  摘要：

  DOI：
• 作为产物：
  描述：

  N-叔丁氧羰基-L-丙氨酸 在 magnesium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 生成 methyl (S)-4-((tert-butoxycarbonyl)amino)-3-oxopentanoate
  参考文献：
  名称：

  Mansour, Tarek S.; Evans, Colleen A., Synthetic Communications, 1990, vol. 20, # 5, p. 773 - 781

  摘要：

  DOI：

文献信息

• α-Amino acid derived enaminones and their application in the synthesis of N-protected methyl 5-substituted-4-hydroxypyrrole-3-carboxylates and other heterocycles
  作者：Uroš Grošelj、Mojca Žorž、Amalija Golobič、Branko Stanovnik、Jurij Svete

  DOI：10.1016/j.tet.2013.11.008

  日期：2013.12

  simple synthesis of novel N-protected methyl 5-substituted-4-hydroxypyrrole-3-carboxylates, which exist in equilibrium with their 4-oxo tautomers, has been developed in two steps starting from N-protected α-amino acids. The key intermediates are enaminones, which can also be isolated, characterized, and used for the construction of other functionalized heterocycles, before they spontaneously decompose

  的新颖的新的和简单的合成ñ -保护的5-取代-4-羟基吡咯-3-羧酸酯，其存在于与他们的4-氧代互变异构体平衡，已经在从开始的两个步骤被开发ñ -保护的α氨基酸。关键中间体是烯胺酮，其也被分离，表征，并用于其它官能化杂环的结构，才自发分解到吡咯产物。4-羟基吡咯易于部分空中氧化，但是可以有效地烷基化或还原成稳定的多取代的吡咯烷衍生物。
• Macrocyclic broad spectrum antibiotics
  申请人：RQX PHARMACEUTICALS, INC.

  公开号：US10392422B2

  公开（公告）日：2019-08-27

  Provided herein are antibacterial compounds, wherein the compounds in some embodiments have broad spectrum bioactivity. In various embodiments, the compounds act by inhibition of bacterial type 1 signal peptidase (SpsB), an essential protein in bacteria. Pharmaceutical compositions and methods for treatment using the compounds described herein are also provided.

  本文提供的是抗菌化合物，其中的化合物在某些实施方案中具有广谱生物活性。在不同的实施方案中，这些化合物通过抑制细菌 1 型信号肽酶（SpsB）发挥作用，SpsB 是细菌中的一种重要蛋白质。还提供了使用本文所述化合物进行治疗的药物组合物和方法。
• The design and synthesis of inhibitors of dethiobiotin synthetase as potential herbicides
  作者：Alan R Rendina、Wendy S Taylor、Katharine Gibson、George Lorimer、Dennis Rayner、Bruce Lockett、Kevin Kranis、Barry Wexler、Dana Marcovici-Mizrahi、Ayelet Nudelman、Abraham Nudelman、Eileen Marsilii、Hongji Chi、Zdislaw Wawrzak、Joseph Calabrese、Weijun Huang、Jia Jia、Gunter Schneider、Ylva Lindqvist、Guang Yang

  DOI：10.1002/(sici)1096-9063(199903)55:3<236::aid-ps888>3.0.co;2-0

  日期：1999.3

  Dethiobiotin synthetase (DTBS;E.C. 6.6.6.6), the penultimate enzyme in the biosynthesis of the essential vitamin biotin, is a new potential target for novel herbicides. Inhibitors were designed based on mechanistic and structural information. The in-vitro activities of these potential inhibitors versus the bacterial enzyme are reported here. Mimics of 7,8-diaminopelargonic acid (DAPA) or the DAPA carbamate reaction intermediate were substrates or partial substrates for the enzyme. Synergistic binding with ATP was noted with compounds which contained an amino functionality, NMR studies and X-ray structures confirmed that the inhibitors could be phosphorylated by the enzyme. Several series of potential inhibitors were designed to take advantage of this partial substrate activity by generating potentially more tightly bound phosphorylated inhibitors in situ, Structure-activity relationships for these series based on both substrate and inhibitory activity are described herein. An X-ray structure for one of these inhibitors is also discussed. Although considerable potential for inhibitors of this type was demonstrated, none of the compounds reported showed sufficient herbicidal activity to be a commercial proposition. (C) 1999 Society of Chemical Industry.
• The Synthesis of the Vitamers of Biotin
  作者：Abraham Nudelman、Ayelet Nudelman、Dana Marcovici-Mizrahi、Dennis Flint

  DOI：10.1006/bioo.1998.1094

  日期：1998.10

  An efficient synthetic pathway for the preparation of the vitamers of biotin which provides easy access to optically pure KAPA as well as diastereomeric mixtures of DAPA, DTB, and analogs thereof has been developed. (C) 1998 Academic Press.
• MANSOUR, TAREK S.;EVANS, COLLEEN A., SYNTH. COMMUN, 20,(1990) N, C. 773-781
  作者：MANSOUR, TAREK S.、EVANS, COLLEEN A.

  DOI：——

  日期：——