methyl (2R,3aR,6R,7R,7aS)-7-(2,2-dimethylpropanoyloxy)-6-hydroxy-2-[(2S)-3-methoxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]-3,3a,5,6,7,7a-hexahydrofuro[3,2-b]pyran-2-carboxylate | 866748-68-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2R,3aR,6R,7R,7aS)-7-(2,2-dimethylpropanoyloxy)-6-hydroxy-2-[(2S)-3-methoxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]-3,3a,5,6,7,7a-hexahydrofuro[3,2-b]pyran-2-carboxylate
• CAS: 866748-68-7
• 化学式: C₂₃H₃₇NO₁₁
• 分子量: 503.547
• InChiKey: LGTSATVLVJGACI-AQDNBLBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  156
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl (2R,3aR,6R,7R,7aS)-7-(2,2-dimethylpropanoyloxy)-6-hydroxy-2-[(2S)-3-methoxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]-3,3a,5,6,7,7a-hexahydrofuro[3,2-b]pyran-2-carboxylate 在 盐酸 作用下， 反应 18.0h， 以95%的产率得到Neodysiherbaine hydrochloride
  参考文献：
  名称：

  Synthesis of neodysiherbaine

  摘要：

  The stereocontrolled synthesis of neodysiherbaine from diacetyl-L-arabinal is described. Key steps in the synthesis include the use of an asymmetric phase-transfer catalyzed glycine imine alkylation to introduce the alpha-amino acid function, and the RuO4-mediated oxidative cyclization of a 1,5-diene to generate the 2,7-dioxabicyclo[4.3.0]nonane ring system. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.07.159
• 作为产物：
  描述：

  1-O'-tert-butyl 2-O'-methyl (2R,2'S,3aR,6S,7R,7aS)-6-acetyloxy-7-(2,2-dimethylpropanoyloxy)-5'-oxospiro[3,3a,5,6,7,7a-hexahydrofuro[3,2-b]pyran-2,4'-pyrrolidine]-1',2'-dicarboxylate 在 sodium tetrahydroborate 、 potassium carbonate 、 pyridinium chlorochromate 作用下， 以 甲醇 、 苯 为溶剂， 反应 54.17h， 生成 methyl (2R,3aR,6R,7R,7aS)-7-(2,2-dimethylpropanoyloxy)-6-hydroxy-2-[(2S)-3-methoxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]-3,3a,5,6,7,7a-hexahydrofuro[3,2-b]pyran-2-carboxylate
  参考文献：
  名称：

  Synthesis of neodysiherbaine

  摘要：

  The stereocontrolled synthesis of neodysiherbaine from diacetyl-L-arabinal is described. Key steps in the synthesis include the use of an asymmetric phase-transfer catalyzed glycine imine alkylation to introduce the alpha-amino acid function, and the RuO4-mediated oxidative cyclization of a 1,5-diene to generate the 2,7-dioxabicyclo[4.3.0]nonane ring system. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.07.159

文献信息

• Synthesis of neodysiherbaine
  作者：Barry Lygo、Daniel Slack、Claire Wilson

  DOI：10.1016/j.tetlet.2005.07.159

  日期：2005.9

  The stereocontrolled synthesis of neodysiherbaine from diacetyl-L-arabinal is described. Key steps in the synthesis include the use of an asymmetric phase-transfer catalyzed glycine imine alkylation to introduce the alpha-amino acid function, and the RuO4-mediated oxidative cyclization of a 1,5-diene to generate the 2,7-dioxabicyclo[4.3.0]nonane ring system. (c) 2005 Elsevier Ltd. All rights reserved.