(2S)-2-[(2R)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]-2H-furan-5-one | 1370655-22-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (2S)-2-[(2R)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]-2H-furan-5-one
• CAS: 1370655-22-3
• 化学式: C₂₃H₂₈O₃Si
• 分子量: 380.559
• InChiKey: JERIMTJQKZCBKY-NQIIRXRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyllithium lithium bromide 、 (2S)-2-[(2R)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]-2H-furan-5-one 在 copper(l) iodide 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 (4S,5S)-5-[(2R)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]-4-methyloxolan-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
• 作为产物：
  描述：

  在 氢气 作用下， 以 甲醇 为溶剂， 反应 11.0h， 以96%的产率得到(2S)-2-[(2R)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]-2H-furan-5-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.