L-铝离子-1,4-内酯 | 78184-43-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: L-铝离子-1,4-内酯
• 英文名称: L-mannonic γ-lactone
• 英文别名: L-allono-1,4-lactone；L-allonic acid-4-lactone；L-Allonsaeure-4-lacton；D-Talonsaeure-γ-lacton；(3S,4R,5S)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-one
• CAS: 78184-43-7
• 化学式: C₆H₁₀O₆
• 分子量: 178.142
• InChiKey: SXZYCXMUPBBULW-QTBDOELSSA-N

物化性质

• 沸点：
  467.9±18.0 °C(Predicted)
• 密度：
  1.766±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  L-铝离子-1,4-内酯 在 sodium amalgam 、 硫酸 、 水 、 溶剂黄146 作用下， 生成 L-ribo-[2]hexosulose bis-phenylhydrazone
  参考文献：
  名称：

  The Preparation of Two New Crystalline Aldohexoses, l-Allose and l-Altrose, from l-Ribose by the Cyanohydrin Reaction^1,2,3

  摘要：

  DOI：

  10.1021/ja01320a048
• 作为产物：
  描述：

  L-arabo-ascorbic acid 在 palladium on activated charcoal 、 氢气 作用下， 生成 L-铝离子-1,4-内酯
  参考文献：
  名称：

  Yadav, Ram Naresh; Banik, Indrani; Banik, Bimal Krishna, Journal of the Indian Chemical Society, 2018, vol. 95, # 11, p. 1393 - 1396

  摘要：

  DOI：

文献信息

• Preparation and Structure−Activity Relationship of Novel P1/P1‘-Substituted Cyclic Urea-Based Human Immunodeficiency Virus Type-1 Protease Inhibitors
  作者：David A. Nugiel、Kim Jacobs、Tabitha Worley、Mona Patel、Robert F. Kaltenbach、Dayton T. Meyer、Prabhakar K. Jadhav、George V. De Lucca、Thomas E. Smyser、Ronald M. Klabe、Lee T. Bacheler、Marlene M. Rayner、Steven P. Seitz

  DOI：10.1021/jm960083n

  日期：1996.1.1

  A series of novel P1/P1'-substituted cyclic urea-based HIV-1 protease inhibitors was prepared. Three different synthetic schemes were used to assemble these compounds. The first approach uses amino acid-based starting materials and was originally used to prepare DMP 323. The other two approaches use L-tartaric acid or L-mannitol as the starting material. The required four contiguous R,S,S,R centers of the cyclic urea scaffold are introduced using substrate control methodology. Each approach has specific advantages based on the desired P1/P1' substituent. Designing analogs based on the enzyme's natural substrates provided compounds with reduced activity. Attempts at exploiting hydrogen bond sites in the S1/S1' pocket, suggested by molecular modeling studies, were not fruitful. Several analogs had better binding affinity compared to our initial leads. Modulating the compound's physical properties led to a 10-fold improvement in translation resulting in better overall antiviral activity.
• An efficient synthesis of l-allono-1,4-lactone from 2,3:5,6-di-O-isopropylidene-d-mannono-1,4-lactone
  作者：Tzenge-Lien Shih、Jui-Huang Tseng

  DOI：10.1016/j.tetlet.2003.12.113

  日期：2004.2

  We reported herein an efficient synthesis of L-allono-1,4-lactone from 2,3:5,6-di-O-isopropylidene-D-inannono-1,4-lactone in five steps. The key feature of this method involved a one-pot, 6 double inversion' procedure at the stereocenters of C-4 and C-5 Of D-mannono- 1,4-lactone to afford the target molecule. (C) 2004 Elsevier Ltd. All rights reserved.
• Humoller; McManus; Austin, Journal of the American Chemical Society, 1936, vol. 58, p. 2481
  作者：Humoller、McManus、Austin

  DOI：——

  日期：——
• Humoller, R.L.Whistler,M.L.Wolfrom Methods in Carbohydrate Chemistry, Bd.1<New York 1962>S.105
  作者：Humoller

  DOI：——

  日期：——
• The Preparation of Two New Crystalline Aldohexoses, l-Allose and l-Altrose, from l-Ribose by the Cyanohydrin Reaction^1,2,3
  作者：W. C. Austin、Fred L. Humoller

  DOI：10.1021/ja01320a048

  日期：1934.5