methyl (7S)-7-[tert-butyl(dimethyl)silyl]oxy-3-oxooctanoate | 137449-13-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: methyl (7S)-7-[tert-butyl(dimethyl)silyl]oxy-3-oxooctanoate
• CAS: 137449-13-9
• 化学式: C₁₅H₃₀O₄Si
• 分子量: 302.486
• InChiKey: CZTODONAVTYLLR-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (7S)-7-[tert-butyl(dimethyl)silyl]oxy-3-oxooctanoate 在 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 生成 ((S)-2-Hydroxy-6-methyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester
  参考文献：
  名称：

  Synthesis of 1,3-dioxin-4-ones having chiral hydroxyalkyl groups at the 6-position by means of baker's yeast reduction and their uses for epc synthesis

  摘要：

  Prochiral methyl ketones connected with 6-(4-oxo-1,3-dioxinyl) group directly or through methylene chain (1-3) gave, by treatment with fermenting baker's yeast, the corresponding (S)-alcohols which served as synthons for a variety of enantiomerically pure compounds.

  DOI：

  10.1016/s0040-4020(01)86552-2
• 作为产物：
  描述：

  (S)-6-(4-Hydroxypentyl)-2,2-dimethyl-1,3-dioxin-4-one 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 methyl (7S)-7-[tert-butyl(dimethyl)silyl]oxy-3-oxooctanoate
  参考文献：
  名称：

  Synthesis of 1,3-dioxin-4-ones having chiral hydroxyalkyl groups at the 6-position by means of baker's yeast reduction and their uses for epc synthesis

  摘要：

  Prochiral methyl ketones connected with 6-(4-oxo-1,3-dioxinyl) group directly or through methylene chain (1-3) gave, by treatment with fermenting baker's yeast, the corresponding (S)-alcohols which served as synthons for a variety of enantiomerically pure compounds.

  DOI：

  10.1016/s0040-4020(01)86552-2

文献信息

• Studies toward the total synthesis of (+)-ptilomycalin A. Use of a tethered Biginelli condensation for the preparation of an advanced tricyclic intermediate
  作者：Larry E. Overman、Michael H. Rabinowitz

  DOI：10.1021/jo00064a007

  日期：1993.6

  An intramolecular ureidoaldehyde condensation, 16 + (R)-14 --> 19, is the key step in a seven-step preparation of the enantiopure spirotricycle 23, a potential intermediate for the enantioselective total synthesis of ptilomycalin A.
• Synthesis of 1,3-dioxin-4-ones having chiral hydroxyalkyl groups at the 6-position by means of baker's yeast reduction and their uses for epc synthesis
  作者：Jun-ichi Sakaki、Yoshiaki Sugita、Masayuki Sato、Chikara Kaneko

  DOI：10.1016/s0040-4020(01)86552-2

  日期：1991.8

  Prochiral methyl ketones connected with 6-(4-oxo-1,3-dioxinyl) group directly or through methylene chain (1-3) gave, by treatment with fermenting baker's yeast, the corresponding (S)-alcohols which served as synthons for a variety of enantiomerically pure compounds.