trifluoroethyl levulinate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: trifluoroethyl levulinate
• 英文别名: Trifluoroethyllevulinate；2,2,2-trifluoroethyl 4-oxopentanoate
• 化学式: C₇H₉F₃O₃
• 分子量: 198.142
• InChiKey: HRDQBZCRGZLAOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  trifluoroethyl levulinate 在 Candida antarctica lipase 、 Sikkon 、 camphor-10-sulfonic acid 作用下， 以 四氢呋喃 为溶剂， 反应 100.0h， 生成 benzyl 3,4-O-isopropylidene-6-O-levulinoyl-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  Human milk oligosaccharides: an enzymatic protection step simplifies the synthesis of 3′- and 6′-O-sialyllactose and their analogues

  摘要：

  We describe a chemo-enzymatic synthesis of 3'- and 6'-O-sialyllactose, two trisaccharides occurring in the 'acidic fraction' of the human milk oligosaccharides and endowed with potential antiadhesive activity. The key step is the highly regioselective 6'-O-acylation of benzyllactoside, which gave access to suitably protected lactose building blocks to be used as acceptors in the sialylation reaction. Moreover, the synthesis of the carboxymethyl and sulfo analogues of the title compounds is reported. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00016-2
• 作为产物：
  描述：

  2,2,2-三氟乙醇 、 6-庚炔酸 在 1,3-双(2,6-二-异丙基苯基)咪唑-2-亚基金(I)氯化物 、 甲烷磺酸 作用下， 以86 %的产率得到trifluoroethyl levulinate
  参考文献：
  名称：

  六氟异丙醇 (HFIP) 作为金催化环异构化和顺序转化中的多功能试剂

  摘要：

  尽管金催化在当代有机合成中具有独特的地位，但该研究领域因需要活化剂和/或添加剂来通过产生阳离子形式的金催化剂来实现催化作用而臭名昭著。环异构化反应占据了金催化反应空间的很大一部分，同时它们代表了合成中经常使用的不同反应家族。在此，六氟异丙醇（HFIP）被证明是金催化环异构化的一种独特简单的工具，使得外部活化剂的使用变得过时，并在某些情况下产生具有 ppm 级催化剂负载的高活性催化系统。HFIP 具有溶剂和活化剂的双重作用，通过通过氢键动态激活 Au-Cl 键，从而启动催化循环。这种特殊的催化模式可以使炔丙酰胺和炔酸与简单的[AuCl(L)]配合物发生高效且可规模化的环化反应。已经对辅助配体和抗衡阴离子进行了彻底的筛选，确立了这种方法作为精细配体/催化剂设计和活化剂使用的替代方法。此外，这一概念还应用于生成 2 H-色烯的 C-C 键形成环异构化反应，以及用于连续或一锅转化的催化系统设计，生成活化的酮酯（一种功能化的N）

  DOI：

  10.1021/acscatal.3c01660

文献信息

• Regioselective esterification of polyhydroxylated steroids by Candida antarctica lipase B
  作者：Anna Bertinotti、Giacomo Carrea、Gianluca Ottolina、Sergio Riva

  DOI：10.1016/s0040-4020(01)89326-1

  日期：1994.1

  polyhydroxylated steroids has been systematically investigated. The enzyme showed a mark preference forthe alcoholic moieties on the A ring and on the steroidal side chain, making it possible the selective acylation at the positions 3 or 21 of polyhydroxy steroids. Acylation with the synthetically useful ester choloroacetate and levulinate was also accomplished, whereas esterification with benzoate and

  已经系统地研究了南极假丝酵母脂肪酶B对多羟基化类固醇乙酰化的区域选择性。该酶显示出对A环和甾体侧链上的醇部分的标记偏爱，使得在多羟基甾体的3或21位选择性酰化成为可能。还完成了用合成上有用的酯氯乙酸酯和乙酰丙酸酯的酰化反应，而用苯甲酸酯和新戊酸酯的酯化未成功。
• Lipase-Catalysed Regioselective Acylations in Combination with Regioselective Glycosylations as a Strategy for the Synthesis of Oligosaccharides: Synthesis of a Series of Fucosyllactose Building Blocks
  作者：Anna Rencurosi、Laura Poletti、Giovanni Russo、Luigi Lay

  DOI：10.1002/ejoc.200200425

  日期：2003.5

  A family of five regioisomeric protected fucosyllactoses has been synthesised in only 14 overall steps from the easily available benzyllactoside. The adopted strategy combines enzymatic regioselective protection, introduction of orthogonal protecting groups and regioselective glycosylations on partially unprotected lactosidic acceptors. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany,

  从易于获得的苄基乳糖苷中，仅用 14 个总步骤就合成了一个由五个区域异构体保护的岩藻糖基乳糖家族。所采用的策略结合了酶促区域选择性保护、正交保护基团的引入和部分未保护乳糖苷受体的区域选择性糖基化。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Selective lipase-catalyzed acylation of 4,6-o-benzylidene-d-glucopyranosides to synthetically useful esters
  作者：Luigi Panza、Sara Brasca、Sergio Riva、Giovanni Russo

  DOI：10.1016/s0957-4166(00)80134-2

  日期：1993.5

  Simple and regioselective lipase-catalyzed acylation of compounds 1 and 4 with synthetically useful esters such as benzoates, chloroacetates, pivaloates and levulinates is described.
• US8486534B2
  申请人：——

  公开号：US8486534B2

  公开（公告）日：2013-07-16
• Human milk oligosaccharides: an enzymatic protection step simplifies the synthesis of 3′- and 6′-O-sialyllactose and their analogues
  作者：Anna Rencurosi、Laura Poletti、Marco Guerrini、Giovanni Russo、Luigi Lay

  DOI：10.1016/s0008-6215(02)00016-2

  日期：2002.3

  We describe a chemo-enzymatic synthesis of 3'- and 6'-O-sialyllactose, two trisaccharides occurring in the 'acidic fraction' of the human milk oligosaccharides and endowed with potential antiadhesive activity. The key step is the highly regioselective 6'-O-acylation of benzyllactoside, which gave access to suitably protected lactose building blocks to be used as acceptors in the sialylation reaction. Moreover, the synthesis of the carboxymethyl and sulfo analogues of the title compounds is reported. (C) 2002 Elsevier Science Ltd. All rights reserved.