(+)-(2R,3S)-4-(tert-butyldimethylsilyloxy)-1-butanoyloxy-2,3-butan-1-ol | 308797-47-9

• 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: (+)-(2R,3S)-4-(tert-butyldimethylsilyloxy)-1-butanoyloxy-2,3-butan-1-ol
• 英文别名: [(2R,3S)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]oxiran-2-yl]methyl butanoate
• CAS: 308797-47-9
• 化学式: C₁₄H₂₈O₄Si
• 分子量: 288.459
• InChiKey: AQAKUDYPEFWRAE-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  48.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-(2R,3S)-4-(tert-butyldimethylsilyloxy)-1-butanoyloxy-2,3-butan-1-ol 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以92%的产率得到(2R,3S)-2,3-Epoxy-4-(tert-butyldimethylsilyloxy)butan-1-ol
  参考文献：
  名称：

  Influence of ester chain length, enzyme, and physical parameters on lipase-catalysed hydrolyses of meso-oxiranedimethanol esters. Part 2

  摘要：

  A range of meso-oxiranedimethanol diesters were prepared and subjected to hydrolysis by a selection of microbial and porcine-derived lipases. The best chain length was then subjected to a wider range of lipases. The physical reaction parameters were further investigated for the best enzyme/substrate combination. The results revealed the effects of ester chain length, choice of enzyme, and physical reaction parameters on the enzymic hydrolysis. Using a combination of the these three variables, it is demonstrated that this is a versatile approach for the optimisation of an enzymic hydrolysis for a given substrate. Additionally, we also report on an efficient, multigram synthesis of oxiranedimethanol diesters from cheap achiral precursors, their successful enzymic hydrolyses to alcohols in good chemical yield and e.e., and their conversion to synthetically useful aldehydes in high yield. Both enantiomeric series can readily be accessed from a single enzymic hydrolysis result. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00276-7
• 作为产物：
  描述：

  cis-2,3-epoxybutane-1,4-dibutyrate 在 咪唑 、 sodium hydroxide 、 porcine pancreatic lipase 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 (+)-(2R,3S)-4-(tert-butyldimethylsilyloxy)-1-butanoyloxy-2,3-butan-1-ol
  参考文献：
  名称：

  Influence of ester chain length, enzyme, and physical parameters on lipase-catalysed hydrolyses of meso-oxiranedimethanol esters. Part 2

  摘要：

  A range of meso-oxiranedimethanol diesters were prepared and subjected to hydrolysis by a selection of microbial and porcine-derived lipases. The best chain length was then subjected to a wider range of lipases. The physical reaction parameters were further investigated for the best enzyme/substrate combination. The results revealed the effects of ester chain length, choice of enzyme, and physical reaction parameters on the enzymic hydrolysis. Using a combination of the these three variables, it is demonstrated that this is a versatile approach for the optimisation of an enzymic hydrolysis for a given substrate. Additionally, we also report on an efficient, multigram synthesis of oxiranedimethanol diesters from cheap achiral precursors, their successful enzymic hydrolyses to alcohols in good chemical yield and e.e., and their conversion to synthetically useful aldehydes in high yield. Both enantiomeric series can readily be accessed from a single enzymic hydrolysis result. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00276-7

文献信息

• Influence of ester chain length, enzyme, and physical parameters on lipase-catalysed hydrolyses of meso-oxiranedimethanol esters. Part 2
  作者：Jonathan D Moseley、James Staunton

  DOI：10.1016/s0957-4166(00)00276-7

  日期：2000.8

  A range of meso-oxiranedimethanol diesters were prepared and subjected to hydrolysis by a selection of microbial and porcine-derived lipases. The best chain length was then subjected to a wider range of lipases. The physical reaction parameters were further investigated for the best enzyme/substrate combination. The results revealed the effects of ester chain length, choice of enzyme, and physical reaction parameters on the enzymic hydrolysis. Using a combination of the these three variables, it is demonstrated that this is a versatile approach for the optimisation of an enzymic hydrolysis for a given substrate. Additionally, we also report on an efficient, multigram synthesis of oxiranedimethanol diesters from cheap achiral precursors, their successful enzymic hydrolyses to alcohols in good chemical yield and e.e., and their conversion to synthetically useful aldehydes in high yield. Both enantiomeric series can readily be accessed from a single enzymic hydrolysis result. (C) 2000 Elsevier Science Ltd. All rights reserved.