(1S,3R,4R,5R)-3,4-O-Benzylidene-1,3,4-trihydroxy-6-oxabicyclo<3.2.1>octan-7-one | 216662-57-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1S,3R,4R,5R)-3,4-O-Benzylidene-1,3,4-trihydroxy-6-oxabicyclo<3.2.1>octan-7-one
• 英文别名: (1S,3R,4R,5R)-4,5-Benzylidenedioxy-1-hydroxycyclohexane-1,3-carbolactone；(1R,2R,6R,8S)-8-hydroxy-4-phenyl-3,5,10-trioxatricyclo[6.2.1.02,6]undecan-9-one；O⁴,O⁵-Benzyliden-chinid
• CAS: 216662-57-6
• 化学式: C₁₄H₁₄O₅
• 分子量: 262.262
• InChiKey: CABHUIHIQVPQJH-ZTWVNJBMSA-N

物化性质

• 沸点：
  480.7±45.0 °C(Predicted)
• 密度：
  1.435±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  quinic acid 、 对甲苯磺酸一水合物 在 苯甲醛 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 以10.8 g (40%)的产率得到(1S,3R,4R,5R)-3,4-O-Benzylidene-1,3,4-trihydroxy-6-oxabicyclo<3.2.1>octan-7-one
  参考文献：
  名称：

  Neuraminidase inhibitors

  摘要：

  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。

  公开号：

  US06593314B1

文献信息

• Synthesis of (2R)-2-bromodehydroquinic acid and (2R)-2-fluorodehydroquinic acid
  作者：Michael K. Manthey、Concepción González-Bello、Chris Abell

  DOI：10.1039/a606104d

  日期：——

  (2R)-2-Bromodehydroquinic acid and (2R)-2-fluorodehydroquinic acid† have each been synthesised in six steps from quinic acid via the common intermediate 6. The syntheses exploit the selective protection of the 4-hydroxy group of the quinic acid lactone 3 with tert-butyldimethylsilyl chloride.

  (2R)-2-溴去氢奎宁酸和(2R)-2-氟去氢奎宁酸†分别是由奎宁酸通过共同的中间体 6 分六个步骤合成的。这些合成利用了叔丁基二甲基氯硅烷对醌内酯 3 的 4-羟基的选择性保护。
• A novel efficient and versatile route to the synthesis of 5-O-feruloylquinic acids
  作者：Candice Menozzi Smarrito、Caroline Munari、Fabien Robert、Denis Barron

  DOI：10.1039/b719132d

  日期：——

  A novel synthesis of 5-O-feruloylquinic acid, a polyphenolic compound found in coffee beans, and its methyl ester derivative has been optimized. The sequence involves 6 steps and is compatible with the preparation of potential human metabolites of these compounds. The key reaction is a Knoevenagel condensation of 4-hydroxy-3-methoxy-benzaldehyde and a malonate ester of quinic acid.

  优化了5-O-阿魏酰奎尼酸（一种在咖啡豆中发现的多酚化合物）及其甲酯衍生物的合成方法。该序列涉及6个步骤，与这些化合物潜在的人类代谢产物的制备兼容。关键反应是4-羟基-3-甲氧基-苯甲醛与奎宁酸的丙二酸酯的Knoevenagel缩合反应。
• Studies directed towards the synthesis of immunosuppressive agent FK-506: synthesis of the entire top-half
  作者：A.V. Rama Rao、T.K. Chakraborty、D Sankaranayanan、A.V. Purandare

  DOI：10.1016/s0040-4039(00)79493-7

  日期：1991.1

  An efficient approach has been developed to construct the entire TOP-HALF of FK-506 involving Grignard reaction of a C-29 bromide with a C-27 methylketo fragment.

  已经开发出一种有效的方法来构建FK-506的整个TOP-HALF，涉及C-29溴化物与C-27甲基酮片段的格氏反应。
• 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.
• Haller, Bernd-Uwe; Kruber, Susanne; Maier, Martin E., Journal fur Praktische Chemie - Chemiker-Zeitung, 1998, vol. 340, # 7, p. 656 - 661
  作者：Haller, Bernd-Uwe、Kruber, Susanne、Maier, Martin E.

  DOI：——

  日期：——