(R)-O-butanoyl-(n-butyl)lactate

• 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: (R)-O-butanoyl-(n-butyl)lactate
• 英文别名: butyl (R)-O-butanoyllactate；butyl O-butyryl-D-lactate；[(2R)-1-butoxy-1-oxopropan-2-yl] butanoate
• 化学式: C₁₁H₂₀O₄
• 分子量: 216.277
• InChiKey: NORZZKKLCYMBBF-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  O-丁酰基乳酸丁酯 在 Novozym-435 作用下， 以 正丁醇 为溶剂， 反应 23.0h， 以99%的产率得到
  参考文献：
  名称：

  [EN] LACTATE PRODUCTION PROCESS
  [FR] PROCÉDÉ DE PRODUCTION DE LACTATE

  摘要：

  提供一种制备化合物(I)的方法。该方法包括在存在Candida antarctica脂肪酶B酶的情况下，通过反应含有化合物(IIA)和化合物(IIB)的混合物与烷基醇来制备含有化合物(I)和化合物(IIB)的产物；其中R1为C1至C6烷基；R2为H或C1至C12烷基。还提供了生产R-乳酸、寡聚R-乳酸、R,R-内酯、聚R-乳酸、烷基S-乳酸、S-乳酸、寡聚S-乳酸、S,S-内酯、聚S-乳酸和立体复合聚乳酸的方法。

  公开号：

  WO2014045036A1

文献信息

• Highly Enantioselective Acylation of <i>rac</i>-Alkyl Lactates Using <i>Candida antarctica</i> Lipase B
  作者：Yeon Soo Lee、Joo Hee Hong、Nan Young Jeon、Keehoon Won、Bum Tae Kim

  DOI：10.1021/op0498722

  日期：2004.11.1

  cases, only alkyl (R)-lactate was stereoselectively acylated at >99.5% ee. The lipase-catalyzed acylation rate of the alkyl lactates was affected by the nature of the organic solvents, but showed no correlation to log P of the solvent. The lipase-catalyzed acylation rate of the alkyl lactates was enhanced by increasing the chain length of the vinyl alkanoate from acetyl to butanoyl and by raising the

  通过在温和条件下使用南极假丝酵母脂肪酶 B，已经完成了来自外消旋混合物的 (R)-乳酸烷基酯与链烷酸乙烯酯的高度对映选择性酰化。本研究考察了有机溶剂、乳酸烷基酯和链烷酸乙烯酯的烷基链长度、反应温度对对映体过量以及反应速率的影响。在所有情况下，只有 (R)-乳酸烷基酯在 >99.5% ee 时被立体选择性酰化。乳酸烷基酯的脂肪酶催化酰化速率受有机溶剂性质的影响，但与溶剂的 log P 无关。通过增加链烷酸乙烯酯从乙酰基到丁酰基的链长以及将反应温度提高到 65 °C，可以提高乳酸烷基酯的脂肪酶催化的酰化速率。
• Use of lipases for the kinetic resolution of lactic acid esters in heptane or in a solvent free system
  作者：Gaëtan Richard、Katherine Nott、François Nicks、Michel Paquot、Christophe Blecker、Marie-Laure Fauconnier

  DOI：10.1016/j.molcatb.2013.08.015

  日期：2013.12

  Kinetic resolution of D,L-ethyl lactate (D,L-LA-Et) and D,L-butyl lactate (D,L-LA-Bu) was accomplished in the presence of lipases. Transesterification of the lactate esters with alcohols was shown to be poorly enantioselective, with a very low preference toward the L enantiomer. However, esterification of the free hydroxyl function of the lactate esters was much more enantioselective, with an opposite preference toward the D form. Among the 200 combinations screened (substrates and lipases), only two reactions fulfilled the required criteria for an efficient resolution (fast reaction, enantioselectivity ratio higher than 100). The best resolution was obtained by esterification of D,L-LA-Bu with butyric anhydride in the presence of lipase B from Candida antarctica (CAL-B) in heptane (at 30 degrees C): LA-Bu was resolved in 6 h with an initial esterification rate of D-LA-BU of 1.5 g L-1 h(-1) g(EZ)(-1), an enantioselectivity ratio higher than 100, a L substrate consumption lower than 1%, and a final substrate enantiomeric excess superior to 99%. After having demonstrated that neither LA-Bu nor BuAn were inhibitors of CAL-B, the reaction was further improved by carrying it out in a solvent free system, at an elevated temperature (60 degrees C), and at a higher lipase concentration. LA-Bu was resolved in 6h with an initial rate of 7.6g L-1 h(-1) g(EZ)(-1), an enantioselectivity ratio higher than 100, and a final substrate enantiomeric excess of 95%. (C) 2013 Elsevier B.V. All rights reserved.