(+)-(2S,3R)-4-butanoyloxy-2,3-epoxybutan-1-ol | 136258-93-0

• 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: (+)-(2S,3R)-4-butanoyloxy-2,3-epoxybutan-1-ol
• 英文别名: [(2R,3S)-3-(hydroxymethyl)oxiran-2-yl]methyl butanoate
• CAS: 136258-93-0
• 化学式: C₈H₁₄O₄
• 分子量: 174.197
• InChiKey: LIXXIBORDJYLGH-NKWVEPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-(2S,3R)-4-butanoyloxy-2,3-epoxybutan-1-ol 在 TEA 、 二甲基亚砜 、 三氟乙酸酐 作用下， 生成 (2R,3R)-4-butyryloxy-2,3-epoxybutan-1-al
  参考文献：
  名称：

  First total synthesis of optically pure methyl (2Z, 8S, 9R)-8,9-epoxydeca-4,6-diyn-2-en-10-hydroxy-1-oate and its acetate, two naturally-occurring antifeedants

  摘要：

  The first total synthesis of the naturally occurring antifeedants 1a, and 1b is described, starting from optically pure (2S, 3R)-4-butyryloxy-2,3-epoxybutan-1-ol 2. (2R, 3S)-5-Bromo-2,3-epoxy-4-pentyn-1-ol 4 is the key intermediate in the synthesis.

  DOI：

  10.1016/s0040-4039(00)79091-5
• 作为产物：
  描述：

  cis-2,3-epoxybutane-1,4-dibutyrate 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 (+)-(2S,3R)-4-butanoyloxy-2,3-epoxybutan-1-ol
  参考文献：
  名称：

  Synthesis of optically pure cis epoxyalcohols via an enzymatic route; an alternative to the sharpless epoxidation.

  摘要：

  Optically pure (2S, 3R)-4-butyryloxy-2,3-epoxybutan-1-ol 2b and (2R, 3S)-4-tert-butyldiphenylsilyoxy-2,3-epoxybutan-1-ol 5, starting materials for the synthesis of enantiomeric epoxyalcohols 3 and 4 were obtained after enzymatic hydrolysis of meso cis-2,3-epoxybutane-1,4-diol diesters 1b.

  DOI：

  10.1016/0040-4039(91)80682-v

文献信息

• Influence of ester chain length on lipase catalysed hydrolyses of meso-oxiranedimethanol esters
  作者：Jonathan D. Moseley、James Staunton

  DOI：10.1016/s0957-4166(98)00374-7

  日期：1998.10

  A range of meso-oxiranedimethanol diesters have been hydrolysed by a selection of microbial and porcine derived lipases. The results reveal the effects of ester substitution, particularly chain length, on the hydrolyses. General conclusions are made which demonstrate that ester chain length can be 'tuned' to achieve optimum enantiomeric enrichment for a given substrate. (C) 1998 Elsevier Science Ltd. All rights reserved.
• First total synthesis of optically pure methyl (2Z, 8S, 9R)-8,9-epoxydeca-4,6-diyn-2-en-10-hydroxy-1-oate and its acetate, two naturally-occurring antifeedants
  作者：D. Grandjean、P. Pale、J. Chuche

  DOI：10.1016/s0040-4039(00)79091-5

  日期：1992.9

  The first total synthesis of the naturally occurring antifeedants 1a, and 1b is described, starting from optically pure (2S, 3R)-4-butyryloxy-2,3-epoxybutan-1-ol 2. (2R, 3S)-5-Bromo-2,3-epoxy-4-pentyn-1-ol 4 is the key intermediate in the synthesis.
• 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.
• Synthesis of optically pure cis epoxyalcohols via an enzymatic route; an alternative to the sharpless epoxidation.
  作者：D. Grandjean、P. Pale、J. Chuche

  DOI：10.1016/0040-4039(91)80682-v

  日期：1991.6

  Optically pure (2S, 3R)-4-butyryloxy-2,3-epoxybutan-1-ol 2b and (2R, 3S)-4-tert-butyldiphenylsilyoxy-2,3-epoxybutan-1-ol 5, starting materials for the synthesis of enantiomeric epoxyalcohols 3 and 4 were obtained after enzymatic hydrolysis of meso cis-2,3-epoxybutane-1,4-diol diesters 1b.