5-[1-Methyl-2-{(2S,3S,4R,5S)-5-[(2S,3S)-3-((1R,2S)-1-methyl-2-trimethylsilanyloxy-propyl)-oxiranylmethyl]-3,4-bis-trimethylsilanyloxy-tetrahydro-pyran-2-yl}-eth-(E)-ylidene]-5,6-dihydro-cyclopenta[c]furan-4-one | 163914-04-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 5-[1-Methyl-2-{(2S,3S,4R,5S)-5-[(2S,3S)-3-((1R,2S)-1-methyl-2-trimethylsilanyloxy-propyl)-oxiranylmethyl]-3,4-bis-trimethylsilanyloxy-tetrahydro-pyran-2-yl}-eth-(E)-ylidene]-5,6-dihydro-cyclopenta[c]furan-4-one
• CAS: 163914-04-3
• 化学式: C₃₁H₅₄O₇Si₃
• 分子量: 623.022
• InChiKey: YHHIQLTZXBRYEC-JMBLMNPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.21
• 重原子数：
  41.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  79.66
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5-[1-Methyl-2-{(2S,3S,4R,5S)-5-[(2S,3S)-3-((1R,2S)-1-methyl-2-trimethylsilanyloxy-propyl)-oxiranylmethyl]-3,4-bis-trimethylsilanyloxy-tetrahydro-pyran-2-yl}-eth-(E)-ylidene]-5,6-dihydro-cyclopenta[c]furan-4-one 以56%的产率得到5-[2-{(2S,3R,4R,5S)-3,4-Dihydroxy-5-[(2S,3S)-3-((1S,2S)-2-hydroxy-1-methyl-propyl)-oxiranylmethyl]-tetrahydro-pyran-2-yl}-1-methyl-eth-(E)-ylidene]-5,6-dihydro-cyclopenta[c]furan-4-one
  参考文献：
  名称：

  Preparation of E-(2-substituted-1-methylethylidene)indanones derived from monic acid

  摘要：

  Alkylation of the lithium dienolate of the monic acid hydroxamate (3) with o-bromo(bromomethyl) benzene or heteroaromatic derivatives gave alpha-alkylated products (5). This alkylation procedure wa surprisingly catalysed by 4-dimethylaminopyridine. Metal-halogen exchange with t-butyl lithium occurred with concomitant intramolecular cyclisation to give a mixture of the deconjugated ketones (6). Reconjugation with potassium t-butoxide stereoselectively produced with the E-isomer (7). Deprotection gave the monic acid derived ketone (1).

  DOI：

  10.1016/s0040-4039(00)73095-4
• 作为产物：
  描述：

  4-bromofuran-3-carbaldehyde 在 sodium tetrahydroborate 、 potassium tert-butylate 、 叔丁基锂 、 三溴化磷 、 二异丙胺 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 4.25h， 生成 5-[1-Methyl-2-{(2S,3S,4R,5S)-5-[(2S,3S)-3-((1R,2S)-1-methyl-2-trimethylsilanyloxy-propyl)-oxiranylmethyl]-3,4-bis-trimethylsilanyloxy-tetrahydro-pyran-2-yl}-eth-(E)-ylidene]-5,6-dihydro-cyclopenta[c]furan-4-one
  参考文献：
  名称：

  Preparation of E-(2-substituted-1-methylethylidene)indanones derived from monic acid

  摘要：

  Alkylation of the lithium dienolate of the monic acid hydroxamate (3) with o-bromo(bromomethyl) benzene or heteroaromatic derivatives gave alpha-alkylated products (5). This alkylation procedure wa surprisingly catalysed by 4-dimethylaminopyridine. Metal-halogen exchange with t-butyl lithium occurred with concomitant intramolecular cyclisation to give a mixture of the deconjugated ketones (6). Reconjugation with potassium t-butoxide stereoselectively produced with the E-isomer (7). Deprotection gave the monic acid derived ketone (1).

  DOI：

  10.1016/s0040-4039(00)73095-4