2-(2-Bromo-benzyl)-3-{(2S,3S,4R,5S)-5-[(2S,3S)-3-((1R,2S)-1-methyl-2-trimethylsilanyloxy-propyl)-oxiranylmethyl]-3,4-bis-trimethylsilanyloxy-tetrahydro-pyran-2-ylmethyl}-but-3-enoic acid methoxy-methyl-amide | 163913-93-7

• 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: 2-(2-Bromo-benzyl)-3-{(2S,3S,4R,5S)-5-[(2S,3S)-3-((1R,2S)-1-methyl-2-trimethylsilanyloxy-propyl)-oxiranylmethyl]-3,4-bis-trimethylsilanyloxy-tetrahydro-pyran-2-ylmethyl}-but-3-enoic acid methoxy-methyl-amide
• CAS: 163913-93-7
• 化学式: C₃₅H₆₂BrNO₇Si₃
• 分子量: 773.04
• InChiKey: DCSDLKLXNXEBOF-GOGMFMMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.06
• 重原子数：
  47.0
• 可旋转键数：
  17.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  78.99
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-(2-Bromo-benzyl)-3-{(2S,3S,4R,5S)-5-[(2S,3S)-3-((1R,2S)-1-methyl-2-trimethylsilanyloxy-propyl)-oxiranylmethyl]-3,4-bis-trimethylsilanyloxy-tetrahydro-pyran-2-ylmethyl}-but-3-enoic acid methoxy-methyl-amide 在 叔丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以86%的产率得到(R)-2-(1-{(2S,3S,4R,5S)-5-[(2S,3S)-3-((1R,2S)-1-Methyl-2-trimethylsilanyloxy-propyl)-oxiranylmethyl]-3,4-bis-trimethylsilanyloxy-tetrahydro-pyran-2-ylmethyl}-vinyl)-indan-1-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：

  (E)-4-{(2S,3R,4R,5S)-3,4-Dihydroxy-5-[(2S,3S)-3-((1S,2S)-2-hydroxy-1-methyl-propyl)-oxiranylmethyl]-tetrahydro-pyran-2-yl}-3-methyl-but-2-enoic acid methoxy-methyl-amide 在 4-二甲氨基吡啶 叔丁基锂 、 三乙胺 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 2-(2-Bromo-benzyl)-3-{(2S,3S,4R,5S)-5-[(2S,3S)-3-((1R,2S)-1-methyl-2-trimethylsilanyloxy-propyl)-oxiranylmethyl]-3,4-bis-trimethylsilanyloxy-tetrahydro-pyran-2-ylmethyl}-but-3-enoic acid methoxy-methyl-amide
  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