(1R,3S,4S,5R)-3-bromo-1-hydroxy-7-oxo-6-oxabicyclo[3.2.1]oct-4-yl benzoate | 105539-78-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,3S,4S,5R)-3-bromo-1-hydroxy-7-oxo-6-oxabicyclo[3.2.1]oct-4-yl benzoate
• 英文别名: 1(R)-4-exo-(benzoyloxy)-3-endo-bromo-1-hydroxy-6-oxabicyclo-[3.2.1]oktan-7-one；[(1R,3S,4S,5R)-3-bromo-1-hydroxy-7-oxo-6-oxabicyclo[3.2.1]octan-4-yl] benzoate
• CAS: 105539-78-4
• 化学式: C₁₄H₁₃BrO₅
• 分子量: 341.158
• InChiKey: XXZUFZHOWAVZLD-OXIWPEFWSA-N

物化性质

• 熔点：
  142-143 °C
• 沸点：
  492.3±45.0 °C(Predicted)
• 密度：
  1.67±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,3S,4S,5R)-3-bromo-1-hydroxy-7-oxo-6-oxabicyclo[3.2.1]oct-4-yl benzoate 在 吡啶 、 lithium hydroxide 、 sodium periodate 、 四氧化锇 、 sodium azide 、 N-甲基吲哚酮 、 偶氮二异丁腈 、 三氟化硼乙醚 、 1-methyl-2-chloropyridinium chloride 、 potassium carbonate 、 氯化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 、 苯 为溶剂， 生成 2-(trimethylsilyl)ethyl (3R,4R,5R)-4-(acetylamino)-3-isopropoxy-5-(2-oxoethyl)-1-cyclohexene-1-carboxylate
  参考文献：
  名称：

  Design, synthesis, and neuraminidase inhibitory activity of GS-4071 analogues that utilize a novel hydrophobic paradigm

  摘要：

  Structure-based design has led to the synthesis of a novel analogue of GS-4071. an influenza neuraminidase inhibitor, in which the basic amino group has been replaced by a hydrophobic vinyl group. An X-ray co-crystal structure of the new inhibitor (K-i = 45 nM) bound to the actin e site shows that the vinyl group occupies the same subsite as the amino group in GS-4071. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00732-1
• 作为产物：
  描述：

  (1S,3R,4R,5R)-3,4-O-Benzylidene-1,3,4-trihydroxy-6-oxabicyclo<3.2.1>octan-7-one 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 反应 1.3h， 以76%的产率得到(1R,3S,4S,5R)-3-bromo-1-hydroxy-7-oxo-6-oxabicyclo[3.2.1]oct-4-yl benzoate
  参考文献：
  名称：

  霉菌孢素的合成和绝对构型。施陶丁格反应的新应用

  摘要：

  描述 sommaire du protocole 实验渗透剂 de synthetiser des mycosporines; Eude cristallographique de leur 配置；使用de la反应de Stander

  DOI：

  10.1021/ja00206a059

文献信息

• Application of stereocontrolled aldol coupling to synthesis of segments of immunosuppressants FK-506 and rapamycin
  作者：James D. White、Jörg Deerberg、Steven G. Toske、Takayuki Yakura

  DOI：10.1016/j.tet.2009.06.030

  日期：2009.8

  The sector comprising C24–C34 of FK-506 containing five of the stereogenic centers in this macrolide was synthesized from (−)-quinic acid. Aldol coupling of the C24–C34 unit with a methyl ketone representing C20–C23 of FK-506 proceeded with complete Felkin stereoselectivity to afford the C20–C34 portion of the immunosuppressant. A chelate transition state invoking coordination of a lithium enolate

  由（-）-奎尼酸合成了包含FK-506的C24-C34的区域，该区域在该大环内酯中包含五个立体异构中心。将C24–C34单元与代表FK-506的C20–C23的甲基酮进行Aldol偶联，以完全的Felkin立体选择性进行，得到免疫抑制剂的C20–C34​​部分。提出了一种使烯醇酸锂与三苯甲基醚配位的螯合过渡态来解释这种立体选择性。FK-506的C26-C34部分构建所采用的策略已扩展到雷帕霉素的C34-C42亚基。使用Mukaiyama不对称抗醛醇偶合剂将大环内酯C26-C33片段中C27,28处的邻二醇功能固定到位。
• Neuraminidase inhibitors
  申请人：Abbott Laboratories

  公开号：US06593314B1

  公开（公告）日：2003-07-15

  The present invention provides compounds of formula Ia and Ib or a pharmaceutically acceptable salt, prodrug, or ester thereof, useful in the inhibition of neuraminidase enzymes from disease-causing microorganisms, especially influenza neuraminidase, pharmaceutical formulations containing same, processes and intermediates for preparing said compounds, as well as methods of using said compounds, including preventing and treating diseases caused by microorganisms having said neuraminidase enzyme.

  本发明提供了公式Ia和Ib的化合物，或其药用可接受的盐、前药或酯，用于抑制疾病引起微生物的神经氨酸酶，特别是流感神经氨酸酶，含有相同化合物的药物配方，用于制备所述化合物的过程和中间体，以及使用所述化合物的方法，包括预防和治疗由具有所述神经氨酸酶酶的微生物引起的疾病。
• Enantioselective formal synthesis of (−)-ovalicin using quinic acid as a chiral template
  作者：Achille Barco、Simonetta Benetti、Carmela De Risi、Paolo Marchetti、Gian P. Pollini、Vinicio Zanirato

  DOI：10.1016/s0957-4166(98)00284-5

  日期：1998.8

  the synthesis of (−)-ovalicin was synthesized using (−)-quinic acid as the chiral source, through a series of stereocontrolled and efficient chemical reactions, thus establishing a new, formal synthesis of the natural target. The featuring spirocyclic epoxide function has been installed by internal Williamson ether synthesis using the functionalities originally present at C-1 of (−)-quinic acid after

  通过一系列立体控制和有效的化学反应，以（-）-奎尼酸为手性来源，合成了合成（-）-卵磷脂的关键中间体18，从而建立了天然靶标的新的正式合成方法。经过适当的调整，在C-2处引入必要的官能度之后，通过内部Williamson醚合成，使用最初存在于（-）-奎宁酸C-1处的官能度，安装了具有特征性的螺环环氧官能团。
• Transformations of Quinic Acid. Asymmetric Synthesis and Absolute Configuration of Mycosporin I and Mycosporin-gly
  作者：James D. White、Janice H. Cammack、Kazuhiko Sakuma、Gordon W. Rewcastle、Rexford K. Widener

  DOI：10.1021/jo00117a008

  日期：1995.6

  D-(-)-Quinic acid (1) was converted to the fungal metabolites mycosporin I (2) and mycosporin-gly (13) via the iminophosphorane 64. The latter was prepared in 10 steps from 1 using oxidative bromination of quinide 33 to furnish 41. Reduction of the gamma-lactone, followed by protection of the 1,2-diol, was accompanied by migration of the benzoyl group to yield 43. The latter was oxidized to 47 which underwent displacement by sulfinate to give 59. O-Methylation, followed by reduction of the benzoate, afforded 61. Oxidation of 61 produced 62 which was converted to beta-azido enone 63. Treatment of 63 with triphenylphosphine gave crystalline 64. An aza-Wittig reaction of 64 with glyoxylate and reduction of the resultant imine yielded 68 which, after deprotection, afforded 13. Analogous coupling of 64 with diethyl ketomalonate and subsequent reduction of the ester groups led to 2. Mycosporin I and mycosporin-gly are shown by this sequence to possess S absolute configuration.
• Synthesis of "iso-EPSP" and evaluation of its interaction with chorismate synthase
  作者：Paul A. Bartlett、Uday. Maitra、Paul M. Chouinard

  DOI：10.1021/ja00285a031

  日期：1986.12