(3R,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-vinyl-tetrahydro-pyran-2-one | 142075-83-0

• 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,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-vinyl-tetrahydro-pyran-2-one
• 英文别名: (3R,4S)-4-[tert-butyl(dimethyl)silyl]oxy-3-ethenyloxan-2-one
• CAS: 142075-83-0
• 化学式: C₁₃H₂₄O₃Si
• 分子量: 256.417
• InChiKey: KFGWCWZFSLYUTR-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-vinyl-tetrahydro-pyran-2-one 在 N-氯代丁二酰亚胺 、 氟化氢吡啶 作用下， 以 吡啶 为溶剂， 生成 (3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-[(S)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-4,5-dihydro-isoxazol-5-yl]-tetrahydro-pyran-2-one
  参考文献：
  名称：

  Convergent assembly of aldol linkages. A study of the stereoselective nitrile oxide cycloaddition reaction

  摘要：

  The aldol equivalency of a stereoselective nitrile oxide cycloaddition is exploited in the development of a general synthetic strategy to the polyene macrolide antibiotics. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00981-3
• 作为产物：
  描述：

  (4R,5S)-3-[(2R,3S)-3-[tert-butyl(dimethyl)silyl]oxy-2-ethenyl-5-hydroxypentanoyl]-4-methyl-5-phenyl-1,3-oxazolidin-2-one 在 magnesium,2-methylpropane,bromide 作用下， 以 四氢呋喃 为溶剂， 以97%的产率得到(3R,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-vinyl-tetrahydro-pyran-2-one
  参考文献：
  名称：

  Convergent assembly of aldol linkages. A study of the stereoselective nitrile oxide cycloaddition reaction

  摘要：

  The aldol equivalency of a stereoselective nitrile oxide cycloaddition is exploited in the development of a general synthetic strategy to the polyene macrolide antibiotics. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00981-3

文献信息

• 2-phenyloxazolines as carboxylate precursors - applications to the synthesis of asymmetric branched-chain structures
  作者：Glenn J. McGarvey、Kenneth J. Wilson、Carl E. Shanholtz

  DOI：10.1016/s0040-4039(00)79046-0

  日期：1992.5

  A synthetic approach to the title compounds is presented that features the asymmetric elaboration of a chiral, non-racemic oxazoline followed by a two-step oxidative ring cleavage of the heterocycle to a triamide for further transformation.