ethyl (3S,5S)-5,6-O-isopropylidene-3,5,6-trihydroxyhexanoate | 91312-53-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: ethyl (3S,5S)-5,6-O-isopropylidene-3,5,6-trihydroxyhexanoate
• 英文别名: ethyl (3R,5S)-5,6-O-isopropylidene-3,5,6-trihydroxyhexanoate；ethyl (3R/S,5S)-5,6-O-isopropylidene-3,5,6-trihydroxyhexanoate
• CAS: 91312-53-7；91312-54-8
• 化学式: C₁₁H₂₀O₅
• 分子量: 232.277
• InChiKey: YDNZMIOIJMCEMQ-GKAPJAKFSA-N

物化性质

• 沸点：
  330.8±22.0 °C(predicted)
• 密度：
  1.084±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.84
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl (3S,5S)-5,6-O-isopropylidene-3,5,6-trihydroxyhexanoate 在 咪唑 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-hydroxymethyl-tetrahydro-pyran-2-one
  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
• 作为产物：
  描述：

  ethyl (3R)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-2-[(R)-(4-methylphenyl)sulfinyl]butanoate 在 氢氧化钾 、 氢化铝 、 mercury dichloride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以41%的产率得到ethyl (3S,5S)-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

• 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
• 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：——