methyl 2-[(2R,3S)-2-[tert-butyl(dimethyl)silyl]oxy-5-[(2R,4R,6S)-4-[tert-butyl(dimethyl)silyl]oxy-6-[(1R)-1-methoxy-2-phenylmethoxyethyl]-3,3-dimethyloxan-2-yl]-3-methyl-4-oxopentyl]-3-methyl-4,6-bis[tri(propan-2-yl)silyloxy]benzoate | 1186291-28-0

• 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: methyl 2-[(2R,3S)-2-[tert-butyl(dimethyl)silyl]oxy-5-[(2R,4R,6S)-4-[tert-butyl(dimethyl)silyl]oxy-6-[(1R)-1-methoxy-2-phenylmethoxyethyl]-3,3-dimethyloxan-2-yl]-3-methyl-4-oxopentyl]-3-methyl-4,6-bis[tri(propan-2-yl)silyloxy]benzoate
• CAS: 1186291-28-0
• 化学式: C₆₂H₁₁₂O₁₀Si₄
• 分子量: 1129.91
• InChiKey: JYOWMDCBKVUHRK-NWWDNWDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.22
• 重原子数：
  76
• 可旋转键数：
  30
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl 2-[(2R,3S)-2-[tert-butyl(dimethyl)silyl]oxy-5-[(2R,4R,6S)-4-[tert-butyl(dimethyl)silyl]oxy-6-[(1R)-1-methoxy-2-phenylmethoxyethyl]-3,3-dimethyloxan-2-yl]-3-methyl-4-oxopentyl]-3-methyl-4,6-bis[tri(propan-2-yl)silyloxy]benzoate 在 硼烷四氢呋喃络合物 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.0h， 以82%的产率得到methyl 2-[(2R,3R,4S)-2-[tert-butyl(dimethyl)silyl]oxy-5-[(2R,4R,6S)-4-[tert-butyl(dimethyl)silyl]oxy-6-[(1R)-1-methoxy-2-phenylmethoxyethyl]-3,3-dimethyloxan-2-yl]-4-hydroxy-3-methylpentyl]-3-methyl-4,6-bis[tri(propan-2-yl)silyloxy]benzoate
  参考文献：
  名称：

  Total Synthesis of Irciniastatin A (Psymberin)

  摘要：

  The total synthesis of (+)-iriciniastatin A (psymberin) is reported in 19 steps and 6% overall yield. Key reactions include a highly convergent enolsilane-oxocarbenium Ion union to generate the C8-C25 fragment and a late-stage coupling of a hemiaminal and acid chloride to complete the synthesis.

  DOI：

  10.1021/ol901655e
• 作为产物：
  描述：

  [(2S,4R,6S)-4-[tert-butyl(dimethyl)silyl]oxy-6-[(1R)-1-methoxy-2-phenylmethoxyethyl]-3,3-dimethyloxan-2-yl] acetate 、 methyl 2-[(2R,3S)-2,4-bis[[tert-butyl(dimethyl)silyl]oxy]-3-methylpent-4-enyl]-3-methyl-4,6-bis[tri(propan-2-yl)silyloxy]benzoate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以59%的产率得到methyl 2-[(2R,3S)-2-[tert-butyl(dimethyl)silyl]oxy-5-[(2R,4R,6S)-4-[tert-butyl(dimethyl)silyl]oxy-6-[(1R)-1-methoxy-2-phenylmethoxyethyl]-3,3-dimethyloxan-2-yl]-3-methyl-4-oxopentyl]-3-methyl-4,6-bis[tri(propan-2-yl)silyloxy]benzoate
  参考文献：
  名称：

  Total Synthesis of Irciniastatin A (Psymberin)

  摘要：

  The total synthesis of (+)-iriciniastatin A (psymberin) is reported in 19 steps and 6% overall yield. Key reactions include a highly convergent enolsilane-oxocarbenium Ion union to generate the C8-C25 fragment and a late-stage coupling of a hemiaminal and acid chloride to complete the synthesis.

  DOI：

  10.1021/ol901655e

文献信息

• Total Synthesis of Irciniastatin A (Psymberin)
  作者：Michael T. Crimmins、Jason M. Stevens、Gregory M. Schaaf

  DOI：10.1021/ol901655e

  日期：2009.9.3

  The total synthesis of (+)-iriciniastatin A (psymberin) is reported in 19 steps and 6% overall yield. Key reactions include a highly convergent enolsilane-oxocarbenium Ion union to generate the C8-C25 fragment and a late-stage coupling of a hemiaminal and acid chloride to complete the synthesis.