(4S)-4-benzyl-3-[(2S,3R,8S)-8-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-2-[(3R,4R)-3-phenylmethoxyhexadec-1-en-4-yl]oxytridec-12-enoyl]-1,3-oxazolidin-2-one | 1160163-78-9

• 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: (4S)-4-benzyl-3-[(2S,3R,8S)-8-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-2-[(3R,4R)-3-phenylmethoxyhexadec-1-en-4-yl]oxytridec-12-enoyl]-1,3-oxazolidin-2-one
• CAS: 1160163-78-9
• 化学式: C₅₂H₈₃NO₇Si
• 分子量: 862.319
• InChiKey: SXALPYKETCRCIF-FZHWHTFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.08
• 重原子数：
  61
• 可旋转键数：
  34
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  94.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4S)-4-benzyl-3-[(2S,3R,8S)-8-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-2-[(3R,4R)-3-phenylmethoxyhexadec-1-en-4-yl]oxytridec-12-enoyl]-1,3-oxazolidin-2-one 、 三乙基硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以93%的产率得到(S)-4-benzyl-3-((2S,3R,8S)-2-(((3R,4R)-3-(benzyloxy)hexadec-1-en-4-yl)oxy)-8-((tert-butyldimethylsilyl)oxy)-3-((triethylsilyl)oxy)tridec-12-enoyl)oxazolidin-2-one
  参考文献：
  名称：

  Asymmetric Total Synthesis of Pyranicin

  摘要：

  The asymmetric total synthesis of pyranicin (1) is reported. The butenolide ring was constructed via an asymmetric alkylation/ring-closing metathesis strategy. The three stereocenters in the left-hand tetrahydropyran ring were installed by sequential chiral auxiliary-mediated aldol reactions. Closure of the tetrahydropyran and fusion of the alkyl backbone were affected via a sequential ring-closing metathesis-cross-metathesis strategy.

  DOI：

  10.1021/ol900814w
• 作为产物：
  描述：

  (6S)-6-[tert-butyl(dimethyl)silyl]oxyundec-10-enal 、 (4S)-4-benzyl-3-[2-[(3R,4R)-3-phenylmethoxyhexadec-1-en-4-yl]oxyacetyl]-1,3-oxazolidin-2-one 在 四氯化钛 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以84%的产率得到(4S)-4-benzyl-3-[(2S,3R,8S)-8-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-2-[(3R,4R)-3-phenylmethoxyhexadec-1-en-4-yl]oxytridec-12-enoyl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Asymmetric Total Synthesis of Pyranicin

  摘要：

  The asymmetric total synthesis of pyranicin (1) is reported. The butenolide ring was constructed via an asymmetric alkylation/ring-closing metathesis strategy. The three stereocenters in the left-hand tetrahydropyran ring were installed by sequential chiral auxiliary-mediated aldol reactions. Closure of the tetrahydropyran and fusion of the alkyl backbone were affected via a sequential ring-closing metathesis-cross-metathesis strategy.

  DOI：

  10.1021/ol900814w

文献信息

• Asymmetric Total Synthesis of Pyranicin
  作者：Michael T. Crimmins、Danielle L. Jacobs

  DOI：10.1021/ol900814w

  日期：2009.6.18

  The asymmetric total synthesis of pyranicin (1) is reported. The butenolide ring was constructed via an asymmetric alkylation/ring-closing metathesis strategy. The three stereocenters in the left-hand tetrahydropyran ring were installed by sequential chiral auxiliary-mediated aldol reactions. Closure of the tetrahydropyran and fusion of the alkyl backbone were affected via a sequential ring-closing metathesis-cross-metathesis strategy.