(4R,5S)-3-[(2R,3S,4S,6Z,8E,10R)-11-[tert-butyl(dimethyl)silyl]oxy-4-[(2S,3S,4R)-3-[tert-butyl(dimethyl)silyl]oxy-5-[tert-butyl(diphenyl)silyl]oxy-4-methylpentan-2-yl]-3-hydroxy-10-methoxy-2,6-dimethylundeca-6,8-dienoyl]-4-methyl-5-phenyl-1,3-oxazolidin-2-one | 1370655-47-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (4R,5S)-3-[(2R,3S,4S,6Z,8E,10R)-11-[tert-butyl(dimethyl)silyl]oxy-4-[(2S,3S,4R)-3-[tert-butyl(dimethyl)silyl]oxy-5-[tert-butyl(diphenyl)silyl]oxy-4-methylpentan-2-yl]-3-hydroxy-10-methoxy-2,6-dimethylundeca-6,8-dienoyl]-4-methyl-5-phenyl-1,3-oxazolidin-2-one
• CAS: 1370655-47-2
• 化学式: C₅₈H₉₁NO₈Si₃
• 分子量: 1014.62
• InChiKey: VKAUURIRGPTNCQ-XGLKHDBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.88
• 重原子数：
  70
• 可旋转键数：
  25
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (4R,5S)-3-[(2R,3S,4S,6Z,8E,10R)-11-[tert-butyl(dimethyl)silyl]oxy-4-[(2S,3S,4R)-3-[tert-butyl(dimethyl)silyl]oxy-5-[tert-butyl(diphenyl)silyl]oxy-4-methylpentan-2-yl]-3-hydroxy-10-methoxy-2,6-dimethylundeca-6,8-dienoyl]-4-methyl-5-phenyl-1,3-oxazolidin-2-one 在 锂硼氢 作用下， 以 乙醚 、 水 为溶剂， 反应 1.5h， 以95%的产率得到(2S,3S,4S,6Z,8E,10R)-11-[tert-butyl(dimethyl)silyl]oxy-4-[(2S,3S,4R)-3-[tert-butyl(dimethyl)silyl]oxy-5-[tert-butyl(diphenyl)silyl]oxy-4-methylpentan-2-yl]-10-methoxy-2,6-dimethylundeca-6,8-diene-1,3-diol
  参考文献：
  名称：

  Stereoselective Synthesis of the C₅–C₁₈ Fragment of Halichomycin

  摘要：

  An efficient and convergent synthesis of the C-5-C-18 fragment of halichomycin is reported. Butanolide fragment 6 was readily prepared stereoselectively from (R)-Roche ester through catalyst control; dienylic bromide domain 7 was synthesized from (S)-serine by substrate control. C-5-C-18 fragment 2 was rapidly assembled through a stereoselective alkylation of the butanolide with the dienylic bromide, followed by functional group transformations.

  DOI：

  10.1021/jo202602n
• 作为产物：
  描述：

  (2S,3S,4S,5R)-2-[(2Z,4E,6R)-7-[tert-butyl(dimethyl)silyl]oxy-6-methoxy-2-methylhepta-2,4-dienyl]-6-[tert-butyl(diphenyl)silyl]oxy-3,5-dimethylhexane-1,4-diol 在 吡啶 、 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 三氟甲磺酸二丁硼 、 potassium carbonate 、 三乙胺 、 2-碘酰基苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 10.75h， 生成 (4R,5S)-3-[(2R,3S,4S,6Z,8E,10R)-11-[tert-butyl(dimethyl)silyl]oxy-4-[(2S,3S,4R)-3-[tert-butyl(dimethyl)silyl]oxy-5-[tert-butyl(diphenyl)silyl]oxy-4-methylpentan-2-yl]-3-hydroxy-10-methoxy-2,6-dimethylundeca-6,8-dienoyl]-4-methyl-5-phenyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Stereoselective Synthesis of the C₅–C₁₈ Fragment of Halichomycin

  摘要：

  An efficient and convergent synthesis of the C-5-C-18 fragment of halichomycin is reported. Butanolide fragment 6 was readily prepared stereoselectively from (R)-Roche ester through catalyst control; dienylic bromide domain 7 was synthesized from (S)-serine by substrate control. C-5-C-18 fragment 2 was rapidly assembled through a stereoselective alkylation of the butanolide with the dienylic bromide, followed by functional group transformations.

  DOI：

  10.1021/jo202602n

文献信息

• Stereoselective Synthesis of the C₅–C₁₈ Fragment of Halichomycin
  作者：Qingjiang Li、Shiyong Mao、Yuxin Cui、Yanxing Jia

  DOI：10.1021/jo202602n

  日期：2012.4.20

  An efficient and convergent synthesis of the C-5-C-18 fragment of halichomycin is reported. Butanolide fragment 6 was readily prepared stereoselectively from (R)-Roche ester through catalyst control; dienylic bromide domain 7 was synthesized from (S)-serine by substrate control. C-5-C-18 fragment 2 was rapidly assembled through a stereoselective alkylation of the butanolide with the dienylic bromide, followed by functional group transformations.