ethyl (3R/S,5S)-3-O-(tert-butyldimethylsilyl)-5,6-O-isopropylidene-3,5,6-trihydroxyhexanoate | 91312-55-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (3R/S,5S)-3-O-(tert-butyldimethylsilyl)-5,6-O-isopropylidene-3,5,6-trihydroxyhexanoate
• 英文别名: ethyl 3-[tert-butyl(dimethyl)silyl]oxy-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]butanoate
• CAS: 91312-55-9；91312-56-0
• 化学式: C₁₇H₃₄O₅Si
• 分子量: 346.539
• InChiKey: VLFUTHABXITDGA-KZUDCZAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (3R/S,5S)-3-O-(tert-butyldimethylsilyl)-5,6-O-isopropylidene-3,5,6-trihydroxyhexanoate 在 吡啶 、 溶剂黄146 作用下， 反应 13.0h， 生成 (3S,5S)-3-O-(tert-butyldimethylsilyl)-6-(p-tolylsulfonyl)-3,5,6-trihydroxyhexanoic acid δ-lactone
  参考文献：
  名称：

  Synthetic and biological studies of compactin and related compounds. 2. Synthesis of the lactone moiety of compactin

  摘要：

  DOI：

  10.1021/jo00195a023
• 作为产物：
  描述：

  (S)-4-(2-羟乙基)-2,2-二甲基-1,3-二氧戊环 在 咪唑 、 氢氧化钾 、 草酰氯 、 叔丁基氯化镁 、 二甲基亚砜 、 三乙胺 、 氢化铝 、 mercury dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.25h， 生成 ethyl (3R/S,5S)-3-O-(tert-butyldimethylsilyl)-5,6-O-isopropylidene-3,5,6-trihydroxyhexanoate
  参考文献：
  名称：

  Bakers' yeast oxidation of methyl para-tolylsuifide: Synthesis of a chiral intermediate in the preparation of the mevinic acid-type hypocholestemic agents

  摘要：

  The use of (R)-methyl para-tolylsulfoxide as a chiral auxiliary in a novel synthesis of a key intermediate en route to mevinic acid-type hypocholestemic agents is described. The synthesis is short and simple consisting of eight steps to yield enantiomerically pure beta-silyloxy-delta-lactone. The chiral sulfoxide used in the synthesis was obtained via a straightforward biooxidation of methyl paratolylsulfide using bakers' yeast (Saccharomyces cerevisiae NCYC 73). The biotransformation involves the use of whole cells and affords the sulfoxide in good yield and with high stereoselectivity.

  DOI：

  10.1016/0040-4020(95)00819-t

文献信息

• Beecher, Jean; Brackenridge, Ian; Roberts, Stanley M., Journal of the Chemical Society. Perkin transactions I, 1995, # 13, p. 1641 - 1644
  作者：Beecher, Jean、Brackenridge, Ian、Roberts, Stanley M.、Tang, Jenny、Willetts, Andrew J.

  DOI：——

  日期：——
• Synthetic and biological studies of compactin and related compounds. 2. Synthesis of the lactone moiety of compactin
  作者：Terry Rosen、Michael J. Taschner、Clayton H. Heathcock

  DOI：10.1021/jo00195a023

  日期：1984.10
• Bakers' yeast oxidation of methyl para-tolylsuifide: Synthesis of a chiral intermediate in the preparation of the mevinic acid-type hypocholestemic agents
  作者：Jenny Tang、Ian Brackenridge、Stanley M. Roberts、Jean Beecher、Andrew J. Willetts

  DOI：10.1016/0040-4020(95)00819-t

  日期：1995.11

  The use of (R)-methyl para-tolylsulfoxide as a chiral auxiliary in a novel synthesis of a key intermediate en route to mevinic acid-type hypocholestemic agents is described. The synthesis is short and simple consisting of eight steps to yield enantiomerically pure beta-silyloxy-delta-lactone. The chiral sulfoxide used in the synthesis was obtained via a straightforward biooxidation of methyl paratolylsulfide using bakers' yeast (Saccharomyces cerevisiae NCYC 73). The biotransformation involves the use of whole cells and affords the sulfoxide in good yield and with high stereoselectivity.