(4R)-4-benzyl-3-[(2R,3S,4R,6R)-3-hydroxy-4-methyl-2-phenylmethoxy-6-triethylsilyloxyheptanoyl]-1,3-oxazolidin-2-one | 681830-24-0

• 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: (4R)-4-benzyl-3-[(2R,3S,4R,6R)-3-hydroxy-4-methyl-2-phenylmethoxy-6-triethylsilyloxyheptanoyl]-1,3-oxazolidin-2-one
• CAS: 681830-24-0
• 化学式: C₃₁H₄₅NO₆Si
• 分子量: 555.787
• InChiKey: ABPJPQBVGAABGD-UEKYOSKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.96
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R)-4-benzyl-3-[(2R,3S,4R,6R)-3-hydroxy-4-methyl-2-phenylmethoxy-6-triethylsilyloxyheptanoyl]-1,3-oxazolidin-2-one 在 咪唑 、 甲醇 、 4-二甲氨基吡啶 、 锂硼氢 、 四丙基高钌酸铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.66h， 生成 (2S,4R,6R)-2-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-4-methyl-6-triethylsilanyloxy-heptan-3-one
  参考文献：
  名称：

  Unified Synthesis of C₁₉−C₂₆ Subunits of Amphidinolides B₁, B₂, and B₃ by Exploiting Unexpected Stereochemical Differences in Crimmins' and Evans' Aldol Reactions

  摘要：

  The efficient synthesis of the C-19-C-26 subunit of amphidinolide B-1 and B-2 has been completed using a boron-mediated aldol reaction. The synthesis of the C-19-C-26 subunit of amphidinolide B-3 has also been accomplished through an unexpected anti aldol reaction using a titanium-mediated process. In addition, the first reported examples of a stereochemical discrepancy between the Evans' boron-mediated oxazolidinone and the Crimmins' titanium-mediated oxazolidinethione aldol reactions are disclosed. A working hypothesis is put forth to explain the results.

  DOI：

  10.1021/jo035829l
• 作为产物：
  描述：

  (R)-2-Methyl-4-triethylsilanyloxy-pentanoic acid methyl-((1R,2R)-1-methyl-2-phenyl-2-triethylsilanyloxy-ethyl)-amide 在 四丙基高钌酸铵 正丁基锂 、 ammonia borane 、 N-甲基吲哚酮 、 三氟甲磺酸二丁硼 、 三乙胺 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 16.17h， 生成 (4R)-4-benzyl-3-[(2R,3S,4R,6R)-3-hydroxy-4-methyl-2-phenylmethoxy-6-triethylsilyloxyheptanoyl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Unified Synthesis of C₁₉−C₂₆ Subunits of Amphidinolides B₁, B₂, and B₃ by Exploiting Unexpected Stereochemical Differences in Crimmins' and Evans' Aldol Reactions

  摘要：

  The efficient synthesis of the C-19-C-26 subunit of amphidinolide B-1 and B-2 has been completed using a boron-mediated aldol reaction. The synthesis of the C-19-C-26 subunit of amphidinolide B-3 has also been accomplished through an unexpected anti aldol reaction using a titanium-mediated process. In addition, the first reported examples of a stereochemical discrepancy between the Evans' boron-mediated oxazolidinone and the Crimmins' titanium-mediated oxazolidinethione aldol reactions are disclosed. A working hypothesis is put forth to explain the results.

  DOI：

  10.1021/jo035829l

文献信息

• Unified Synthesis of C₁₉−C₂₆ Subunits of Amphidinolides B₁, B₂, and B₃ by Exploiting Unexpected Stereochemical Differences in Crimmins' and Evans' Aldol Reactions
  作者：Wei Zhang、Rich G. Carter、Alexandre F. T. Yokochi

  DOI：10.1021/jo035829l

  日期：2004.4.1

  The efficient synthesis of the C-19-C-26 subunit of amphidinolide B-1 and B-2 has been completed using a boron-mediated aldol reaction. The synthesis of the C-19-C-26 subunit of amphidinolide B-3 has also been accomplished through an unexpected anti aldol reaction using a titanium-mediated process. In addition, the first reported examples of a stereochemical discrepancy between the Evans' boron-mediated oxazolidinone and the Crimmins' titanium-mediated oxazolidinethione aldol reactions are disclosed. A working hypothesis is put forth to explain the results.