(3R,4R,5R)-4-Hydroxy-3-methyl-5-trimethylsilanyl-dihydro-furan-2-one | 156757-22-1

• 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,4R,5R)-4-Hydroxy-3-methyl-5-trimethylsilanyl-dihydro-furan-2-one
• 英文别名: (3R,4R,5R)-4-hydroxy-3-methyl-5-trimethylsilyloxolan-2-one
• CAS: 156757-22-1
• 化学式: C₈H₁₆O₃Si
• 分子量: 188.299
• InChiKey: JUAXLLZDWVDYBM-ATRFCDNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.79
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4R,5R)-4-Hydroxy-3-methyl-5-trimethylsilanyl-dihydro-furan-2-one 在 咪唑 、 盐酸 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 水 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 生成 (R)-4-tert-butyldimethylsilyloxy-3-methyl-1-butanol
  参考文献：
  名称：

  Synthesis of β-hydroxy-γ-trimethylsilyl-γ-butyrolactone as key chiral building block for preparation of four-carbon chain units having tertiary stereogenic carbon

  摘要：

  A new chiral building block beta-hydroxy-gamma-trimethylsilyl-gamma-butyrolactone (1) was prepared from gamma-trimethylsilylallyl acetate (2) via two steps in excellent overall yield. The lactone 1 is useful precursor to four-carbon chain blocks having tertiary stereogenic center such as 6, 10 and 11.

  DOI：

  10.1016/s0040-4039(00)73364-8
• 作为产物：
  描述：

  3-(trimethylsilyl)-2-propenylacetate 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三苯基膦 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 N,N-二异丙基乙胺 、 sodium bromide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 水 、 叔丁醇 为溶剂， 反应 25.5h， 生成 (3R,4R,5R)-4-Hydroxy-3-methyl-5-trimethylsilanyl-dihydro-furan-2-one
  参考文献：
  名称：

  Synthesis of β-hydroxy-γ-trimethylsilyl-γ-butyrolactone as key chiral building block for preparation of four-carbon chain units having tertiary stereogenic carbon

  摘要：

  A new chiral building block beta-hydroxy-gamma-trimethylsilyl-gamma-butyrolactone (1) was prepared from gamma-trimethylsilylallyl acetate (2) via two steps in excellent overall yield. The lactone 1 is useful precursor to four-carbon chain blocks having tertiary stereogenic center such as 6, 10 and 11.

  DOI：

  10.1016/s0040-4039(00)73364-8

文献信息

• Miyazaki Yasushi, Hotta Hiroyasu, Sato Fumie, Tetrahedron Lett, 35 (1994) N 25, S 4389- 4392
  作者：Miyazaki Yasushi, Hotta Hiroyasu, Sato Fumie

  DOI：——

  日期：——
• Synthesis of β-hydroxy-γ-trimethylsilyl-γ-butyrolactone as key chiral building block for preparation of four-carbon chain units having tertiary stereogenic carbon
  作者：Yasushi Miyazaki、Hiroyasu Hotta、Fumie Sato

  DOI：10.1016/s0040-4039(00)73364-8

  日期：1994.6

  A new chiral building block beta-hydroxy-gamma-trimethylsilyl-gamma-butyrolactone (1) was prepared from gamma-trimethylsilylallyl acetate (2) via two steps in excellent overall yield. The lactone 1 is useful precursor to four-carbon chain blocks having tertiary stereogenic center such as 6, 10 and 11.