(1R,2S,4aR,7S,8aS)-1,2-dimethyl-7-phenyldecahydronaphthalene | 126923-31-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: (1R,2S,4aR,7S,8aS)-1,2-dimethyl-7-phenyldecahydronaphthalene
• CAS: 126923-31-7
• 化学式: C₁₃H₁₆O₅
• 分子量: 252.267
• InChiKey: KRNWQNYQBBRLMC-QWQWKMKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.22
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  68.15
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1R,2S,4aR,7S,8aS)-1,2-dimethyl-7-phenyldecahydronaphthalene 、 溴甲苯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 1.0h， 以96%的产率得到1,5-anhydro-2,3-di-O-benzyl-4,6-O-benzylidene-D-galactitol
  参考文献：
  名称：

  Synthesis of octahydropyrano[3,2-b]pyrrole-2-carboxylic acid derivatives from d-mannose

  摘要：

  Bicyclic amino acids are useful building blocks in synthesizing biologically active molecules and peptidomimetics. 2-Carboxy-6-hydroxyloctahydroindole (Choi) is a novel bicyclic amino acid found in the marine natural products acruginosins. Many compounds in the aeruginosin family exhibit inhibition activities toward scrine proteases including thrombin and trypsin. The unique Choi structure is the common feature of this family of oligopeptides and this motif is important for their observed biological activities. To better understand the influence of the stereochemistry of the Choi core structure on the inhibition activities, we have previously synthesized ring-oxygenated variants from glucose. The preparation of octahydro-pyrano[3,2-b]pyrrole 2-carboxylic acids from D-mannose is reported here. These novel bicyclic amino acids can be used in the preparation of aeruginosin analogs, as well as conformationally constrained peptidomimetics or other biologically active molecules. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.03.017
• 作为产物：
  描述：

  苯甲醛二甲缩醛 、 1,5-anhydro-D-galactitol 在 tetrafluoroboric acid 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 以92%的产率得到(1R,2S,4aR,7S,8aS)-1,2-dimethyl-7-phenyldecahydronaphthalene
  参考文献：
  名称：

  Synthesis of octahydropyrano[3,2-b]pyrrole-2-carboxylic acid derivatives from d-mannose

  摘要：

  Bicyclic amino acids are useful building blocks in synthesizing biologically active molecules and peptidomimetics. 2-Carboxy-6-hydroxyloctahydroindole (Choi) is a novel bicyclic amino acid found in the marine natural products acruginosins. Many compounds in the aeruginosin family exhibit inhibition activities toward scrine proteases including thrombin and trypsin. The unique Choi structure is the common feature of this family of oligopeptides and this motif is important for their observed biological activities. To better understand the influence of the stereochemistry of the Choi core structure on the inhibition activities, we have previously synthesized ring-oxygenated variants from glucose. The preparation of octahydro-pyrano[3,2-b]pyrrole 2-carboxylic acids from D-mannose is reported here. These novel bicyclic amino acids can be used in the preparation of aeruginosin analogs, as well as conformationally constrained peptidomimetics or other biologically active molecules. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.03.017

文献信息

• Regioselective Esterification of Vicinal Diols on Monosaccharide Derivatives via Mitsunobu Reactions
  作者：Guijun Wang、Jean-Rene Ella-Menye、Michael St. Martin、Hao Yang、Kristopher Williams

  DOI：10.1021/ol801316f

  日期：2008.10.2

  esterification reactions of secondary alcohols derived from d-glucose, d-mannose, and d-galactose via the Mitsunobu reaction. The benzoylation reaction of vicinal diols derived from monosaccharides under Mitsunobu conditions afforded monobenzoates with retention of stereochemistry only. The regioselectivity of these reactions depends on the stereochemistry of the sugar starting material. The Mitsunobu reactions

  我们通过Mitsunobu反应进行了一系列衍生自d-葡萄糖，d-甘露糖和d-半乳糖的仲醇的酯化反应。在Mitsunobu条件下衍生自单糖的邻位二醇的邻苯二甲酰化反应提供的单苯甲酸酯只保留了立体化学。这些反应的区域选择性取决于糖原料的立体化学。这些二醇上的Mitsunobu反应可用于选择性保护其他邻位仲羟基。