(3S)-<2,3-(2)H2>-2,4-di-O-benzoyl-3,6-dideoxy-L-mannono-1,5-lactone | 111476-66-5

• 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: (3S)-<2,3-(2)H2>-2,4-di-O-benzoyl-3,6-dideoxy-L-mannono-1,5-lactone
• 英文别名: (3S)-(2,3-(2)H2)-2,4-di-O-benzoyl-3,6-dideoxy-L-mannono-1,5-lactone
• CAS: 111476-66-5
• 化学式: C₂₀H₁₈O₆
• 分子量: 356.343
• InChiKey: GWAJSJIUDSHXOO-CARDURFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3S)-<2,3-(2)H2>-2,4-di-O-benzoyl-3,6-dideoxy-L-mannono-1,5-lactone 在 2,3-二甲基-2-丁烯 、 硼烷四氢呋喃络合物 、 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以65%的产率得到
  参考文献：
  名称：

  A Large Family of Enzymes Responsible for the Modular Architecture of Nematode Pheromones

  摘要：

  The nematode Caenorhabditis elegans produces a broad family of pheromones, known as the ascarosides, that are modified with a variety of groups derived from primary metabolism. These modifications are essential for the diverse activities of the ascarosides in development and various behaviors, including attraction, aggregation, avoidance, and foraging. The mechanism by which these different groups are added to the ascarosides is poorly understood. Here, we identify a family of over 30 enzymes, which are homologous to mammalian carboxylesterase (CES) enzymes, and show that a number of these enzymes are responsible for the selective addition of specific modifications to the ascarosides. Through stable isotope feeding experiments, we demonstrate the in vivo activity of the CES-like enzymes and provide direct evidence that the acyl-CoA synthetase ACS-7, which was previously implicated in the attachment of certain modifications to the ascarosides in C. elegans, instead activates the side chains of certain ascarosides for shortening through beta-oxidation. Our data provide a key to the combinatorial logic that gives rise to different modified ascarosides, which should greatly facilitate the exploration of the specific biological functions of these pheromones in the worm.

  DOI：

  10.1021/jacs.0c04223
• 作为产物：
  描述：

  2,4-di-O-benzoyl-3,6-dideoxy-L-erythro-hex-2-enono-1,5-lactone 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 以80%的产率得到(3S)-<2,3-(2)H2>-2,4-di-O-benzoyl-3,6-dideoxy-L-mannono-1,5-lactone
  参考文献：
  名称：

  立体定向标记的3,6-二脱氧己糖的合成。

  摘要：

  立体定向氘的天链糖（3,6-二脱氧-L-阿拉伯己糖），a糖（3,6-二脱氧-D-木己糖）和半乳糖（3,6-二脱氧-D-核糖己糖）的制备讨论了C-3处的标记。用于合成这些糖的方法，例如烯烃的氢化，卤化物的置换，环氧化物的还原以及甲苯磺酸酯的取代，说明了导致立体定向氘结合的多种策略。此处描述的许多技术应具有普遍性，可用于合成其他氘标记的糖。

  DOI：

  10.1016/0008-6215(90)84227-l

文献信息

• Synthesis of stereospecifically labeled carbohydrates: Preparation of (3S)− and (3R)-[3-2H1]ascarylose
  作者：Oksoo Han、Hung-wen Liu

  DOI：10.1016/s0040-4039(00)95914-8

  日期：1987.1

  The general problem of the synthesis of 3,6-dideoxy sugars containing stereospecifically labeled hydrogen isotope at C-3 is addressed for the specific case of ascarylose (3,6-dideoxy-L-arabino-hexose).

  对于特定的天桥糖（3,6-二脱氧-L-阿拉伯糖基己糖），解决了合成在C-3处含有立体特异性标记的氢同位素的3,6-二脱氧糖的一般问题。
• RUSSELL, RAYMOND N.;WEIGEL, THERESA M.;HAN, OKSOO;LIU, HUNG-WEN, CARBOHYDR. RES., 201,(1990) N, C. 95-114
  作者：RUSSELL, RAYMOND N.、WEIGEL, THERESA M.、HAN, OKSOO、LIU, HUNG-WEN

  DOI：——

  日期：——