(3R,5S)-3-methyl-5-((S)-2,2,3,3,9,9,10,10-octamethyl-4,8-dioxa-3,9-disilaundecan-5-yl)dihydrofuran-2(3H)-one | 1199807-63-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3R,5S)-3-methyl-5-((S)-2,2,3,3,9,9,10,10-octamethyl-4,8-dioxa-3,9-disilaundecan-5-yl)dihydrofuran-2(3H)-one
• 英文别名: (3R,5S)-5-[(1S)-1,3-bis[[tert-butyl(dimethyl)silyl]oxy]propyl]-3-methyloxolan-2-one
• CAS: 1199807-63-0
• 化学式: C₂₀H₄₂O₄Si₂
• 分子量: 402.722
• InChiKey: DIQRKVSWADGYIS-IKGGRYGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.74
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,5S)-3-methyl-5-((S)-2,2,3,3,9,9,10,10-octamethyl-4,8-dioxa-3,9-disilaundecan-5-yl)dihydrofuran-2(3H)-one 在 锂硼氢 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以96%的产率得到(2R,4S,5S)-5,7-bis(tert-butyldimethylsilyloxy)-2-methylheptane-1,4-diol
  参考文献：
  名称：

  Synthesis of the Macrocyclic Core of Iriomoteolide 3a

  摘要：

  The asymmetric synthesis of the fully functionalized macrocyclic core of iriomoteolide 3a, a cytotoxic 15-membered macrolide, Is disclosed. The key steps involve Sharpless asymmetric dihydroxylation, Sharpless asymmetric epoxidation, olefin cross-metathesis, Yamaguchi esterification, and a ring-closing metathesis reaction for macrocyclization.

  DOI：

  10.1021/ol9025183
• 作为产物：
  描述：

  (5S)-5-[(1S)-1,3-bis[[tert-butyl(dimethyl)silyl]oxy]propyl]oxolan-2-one 、 碘甲烷 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以85%的产率得到(3R,5S)-3-methyl-5-((S)-2,2,3,3,9,9,10,10-octamethyl-4,8-dioxa-3,9-disilaundecan-5-yl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Synthesis of the Macrocyclic Core of Iriomoteolide 3a

  摘要：

  The asymmetric synthesis of the fully functionalized macrocyclic core of iriomoteolide 3a, a cytotoxic 15-membered macrolide, Is disclosed. The key steps involve Sharpless asymmetric dihydroxylation, Sharpless asymmetric epoxidation, olefin cross-metathesis, Yamaguchi esterification, and a ring-closing metathesis reaction for macrocyclization.

  DOI：

  10.1021/ol9025183

文献信息

• Synthesis of the Macrocyclic Core of Iriomoteolide 3a
  作者：Chada Raji Reddy、Gajula Dharmapuri、Nagavaram Narsimha Rao

  DOI：10.1021/ol9025183

  日期：2009.12.17

  The asymmetric synthesis of the fully functionalized macrocyclic core of iriomoteolide 3a, a cytotoxic 15-membered macrolide, Is disclosed. The key steps involve Sharpless asymmetric dihydroxylation, Sharpless asymmetric epoxidation, olefin cross-metathesis, Yamaguchi esterification, and a ring-closing metathesis reaction for macrocyclization.