(4S)-3-[(2S,3R,4R,5R,6S)-5-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-2,4,6-trimethyloctanoyl]-4-propan-2-yl-1,3-oxazolidin-2-one | 206651-89-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S)-3-[(2S,3R,4R,5R,6S)-5-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-2,4,6-trimethyloctanoyl]-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 206651-89-0
• 化学式: C₂₃H₄₅NO₅Si
• 分子量: 443.7
• InChiKey: RUXBBDRSTSOXQM-XYWBXWKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S)-3-[(2S,3R,4R,5R,6S)-5-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-2,4,6-trimethyloctanoyl]-4-propan-2-yl-1,3-oxazolidin-2-one 在 lithium aluminium tetrahydride 、 三甲基铝 、 二异丁基氢化铝 、 lithium hexamethyldisilazane 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 (4R,5S,6R,7R,8S,E)-7-(tert-butyldimethylsilyloxy)-2,4,6,8-tetramethyldec-2-ene-1,5-diol
  参考文献：
  名称：

  Total synthesis of callystatin A, a potent cytotoxic polyketide from the marine sponge, Callyspongia truncata

  摘要：

  A first total synthesis of callystatin A (1), a potent cytotoxic polyketide from the marine sponge Callyspongia truncata, has been achieved by use of an E-selective Wittig olefination and asymmetric Evans aldol condensation as the key reactions. Thus, the absolute stereostructure of 1 previously established by us was confirmed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00151-8
• 作为产物：
  描述：

  (S)-2-甲基丁醛 在 2,6-二甲基吡啶 、 三氟甲磺酸二丁硼 、 三甲基铝 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (4S)-3-[(2S,3R,4R,5R,6S)-5-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-2,4,6-trimethyloctanoyl]-4-propan-2-yl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Total synthesis of callystatin A, a potent cytotoxic polyketide from the marine sponge, Callyspongia truncata

  摘要：

  A first total synthesis of callystatin A (1), a potent cytotoxic polyketide from the marine sponge Callyspongia truncata, has been achieved by use of an E-selective Wittig olefination and asymmetric Evans aldol condensation as the key reactions. Thus, the absolute stereostructure of 1 previously established by us was confirmed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00151-8

文献信息

• Total synthesis of callystatin A, a potent cytotoxic polyketide from the marine sponge, Callyspongia truncata
  作者：Nobutoshi Murakami、Weiqi Wang、Masashi Aoki、Yasuhiro Tsutsui、Masanori Sugimoto、Motomasa Kobayashi

  DOI：10.1016/s0040-4039(98)00151-8

  日期：1998.4

  A first total synthesis of callystatin A (1), a potent cytotoxic polyketide from the marine sponge Callyspongia truncata, has been achieved by use of an E-selective Wittig olefination and asymmetric Evans aldol condensation as the key reactions. Thus, the absolute stereostructure of 1 previously established by us was confirmed. (C) 1998 Elsevier Science Ltd. All rights reserved.