(2S,3R)-3-tert-butyldimethylsilyloxymethyl-2-((6R,2E)-7-tert-butyldiphenylsilyloxy-6-methyl-4-methylene-2-hepten-2-yl)-2-methyloxirane | 1330680-49-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R)-3-tert-butyldimethylsilyloxymethyl-2-((6R,2E)-7-tert-butyldiphenylsilyloxy-6-methyl-4-methylene-2-hepten-2-yl)-2-methyloxirane
• 英文别名: tert-butyl-[(E,2R)-6-[(2S,3R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-methyloxiran-2-yl]-2-methyl-4-methylidenehept-5-enoxy]-diphenylsilane
• CAS: 1330680-49-3
• 化学式: C₃₅H₅₄O₃Si₂
• 分子量: 578.983
• InChiKey: KACGRAWHIFNKNA-PKBXLENGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.27
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2R,3S,4E)-2,3-epoxy-3,4-dimethyl-5-triisopropylsilyl-4-penten-1-ol 在 咪唑 、 叔丁基锂 、 bis(pyridine)iodonium tetrafluoroborate 作用下， 以 四氢呋喃 、 二氯甲烷 、 六氟异丙醇 、 正戊烷 为溶剂， 反应 0.33h， 生成 (2S,3R)-3-tert-butyldimethylsilyloxymethyl-2-((6R,2E)-7-tert-butyldiphenylsilyloxy-6-methyl-4-methylene-2-hepten-2-yl)-2-methyloxirane
  参考文献：
  名称：

  Iododesilylation of TIPS-, TBDPS-, and TBS-Substituted Alkenes in Connection with the Synthesis of Amphidinolides B/D

  摘要：

  The C-Si bonds of triisopropylsilyl-substituted alkenes, 1,3-dienes, and related multifunctional substrates, as well as analogous C-TBDPS and C-TBS bonds, are readily and chemoselectively cleaved with NIS (or other sources of I(+), such as N-iodosaccharin, 1,3-diodohydantoin, and Ipy(2)BF(4)). The desired iodoalkenes are obtained stereospecifically without byproducts, provided that the reactions are carried out in CF(3)CHOHCF(3) and, in general, with 30 mol % of Ag(2)CO(3) (or AgOAc/2,6-Iutidine) as an additive. Fragment C10-C18 of cytotoxic amphidinolides B1-B3 and D has been synthesized using this improved procedure.

  DOI：

  10.1021/ol2020187