Ethyl 4-t-butoxy-3-hydroxybutanoate | 106058-89-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: Ethyl 4-t-butoxy-3-hydroxybutanoate
• 英文别名: ethyl 4-(tert-butoxy)-3-hydroxybutanoate；ethyl (i)-4-t-butoxy-3-hydroxybutanoate；4-t-Butoxy-3-hydroxy-butyric acid, ethyl ester；ethyl 3-hydroxy-4-[(2-methylpropan-2-yl)oxy]butanoate
• CAS: 106058-89-3
• 化学式: C₁₀H₂₀O₄
• 分子量: 204.266
• InChiKey: PRVDZTWZVHPSJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl 4-t-butoxy-3-hydroxybutanoate 在 吡啶 、 titanium(IV) tetraethanolate 、 三氟乙酸 作用下， 以 乙醇 为溶剂， 反应 126.0h， 生成 (R)-4-tert-Butoxy-3-(1-ethoxy-ethoxy)-butyric acid ethyl ester
  参考文献：
  名称：

  (R)-Ethyl 4-t-Butoxy-3-hydroxybutanoate, a Versatile Chiral Building Block for EPC (Enantiomerically Pure Compound) Syntheses, by Yeast Reduction of Ethyl 4-t-Butoxy-3-oxobutanoate

  摘要：

  用发酵酵母还原 4-t-丁氧基-3-氧代丁酸乙酯，可得到(R)-4-t-丁氧基-3-羟基丁酸乙酯，纯度为 97%。由于保护基团很容易从还原产物中去除，因此本程序为正式从(R)-苹果酸中提取的 "手性嵌段世界 "提供了一个简单的入口。

  DOI：

  10.1055/s-1986-31468
• 作为产物：
  描述：

  4-叔丁氧基乙酰乙酸乙酯 在 [RhCl2(p-cymene)]2 、 氢气 、 (2,2,2',2'-tetramethyl[4,4'-bibenzo[d][1,3]dioxole]-5,5'-diyl)bis(diphenylphosphine) 作用下， 以 乙醇 为溶剂， 70.0 ℃ 、2.0 MPa 条件下， 反应 18.0h， 生成 Ethyl 4-t-butoxy-3-hydroxybutanoate
  参考文献：
  名称：

  Ru催化γ-杂原子取代的β-酮基酯的不对称加氢

  摘要：

  在Ru- （S）-SunPhos催化剂存在下，通过氢化γ-杂原子取代的β-酮酯，合成了一系列具有高对映选择性（高达99.1％ee）的对映体纯的γ-杂原子取代的β-羟基酯。这些不对称氢化为各种天然存在的生物活性化合物提供了重要的组成部分。

  DOI：

  10.1021/jo201822k

文献信息

• Production method of hexahydrofurofuranol derivative, intermediate therefor and production method thereof
  申请人：Sumika Fine Chemicals Co., Ltd.

  公开号：US20040162340A1

  公开（公告）日：2004-08-19

  The present invention provides a method for producing compound (XIV) useful as an intermediate for pharmaceutical agents efficiently and economically on an industrial scale without using ozone oxidation and highly toxic reagent, and an intermediate used for this method. Particularly, the present invention provides a method for producing a compound having an absolute configuration represented by the formula (XV) and an enantiomer thereof without using a technique such as optical resolution and the like, and an intermediate used for this method. (1) Compound (XIII) as a starting material is led to compound (I), and after introducing a protecting group, subjected to reduction and cyclization to give compound (XIV). Particularly, compound (XIII) as a material is led to compound (I) via compound (XX) to produce compound (XIV). Using an optically active compound (XIII) as a starting material, a compound having an absolute configuration represented by the formula (XV) and the like are produced highly stereoselectively. (2) Compound (XXI) as a starting material is stereoselectively reduced to give compound (XXII), and by introduction of a protecting group, reduction and cyclization, compound (XXVI) is obtained, and by inverting hydroxyl group, compound (XV) is produced. 1 wherein each symbol is as defined in the specification.

  本发明提供了一种在工业规模上高效且经济地生产化合物(XIV)的方法，该化合物可作为制药中间体，无需使用臭氧氧化和高毒性试剂，以及用于该方法的中间体。特别是，本发明提供了一种生产具有由公式(XV)表示的绝对构型及其对映体的化合物的方法，无需使用光学分辨等技术，以及用于该方法的中间体。(1) 以化合物(XIII)为起始材料，引导至化合物(I)，引入保护基团后，进行还原和环化以得到化合物(XIV)。特别是，化合物(XIII)作为原料通过化合物(XX)引导至化合物(I)，以生产化合物(XIV)。使用具有光学活性的化合物(XIII)作为起始材料，高度立体选择性地生产具有由公式(XV)表示的绝对构型等的化合物。(2) 以化合物(XXI)为起始材料，立体选择性地还原得到化合物(XXII)，通过引入保护基团、还原和环化，得到化合物(XXVI)，并通过反转羟基，生产化合物(XV)。其中每个符号的定义如说明书中所述。
• Process for producing optically active gamma-butyrolactone
  申请人：——

  公开号：US20030105341A1

  公开（公告）日：2003-06-05

  This invention provides a novel process for producing optically active 3-hydroxy-&ggr;-butyrolactone in a short step, which is superior economically and in efficiency and industrially suitable by using a starting material which is inexpensive and easily available and reagents easy to handle. This invention relates to a process for producing optically active 3-hydroxy-&ggr;-butyrolactone represented by formula I: 1 wherein the symbol * means an asymmetric carbon atom, which comprises hydrogenating an optically active 4-substituted oxy-3-hydroxybutyrate represented by formula II: 2 wherein R 1 represents a C 1-4 lower alkyl group, R 2 represents a protective group for a hydroxyl group deprotected by hydrogenation with a heterogeneous hydrogenation catalyst, and the symbol * has the same meaning as defined above, in the presence of a heterogeneous hydrogenation catalyst and an acidic substance followed by deprotection and simultaneous ring closure thereof.

  本发明提供了一种新的生产光学活性3-羟基-γ-丁内酯的工艺，该工艺步骤短，经济高效，适合工业应用，使用的起始材料廉价易得，试剂易于处理。本发明涉及一种生产光学活性3-羟基-γ-丁内酯的工艺，其化学式为I:1，其中符号*表示不对称碳原子，包括在异质催化剂和酸性物质的存在下，氢化化合式II:2所代表的光学活性4-取代氧基-3-羟基丁酸酯，其中R1表示C1-4较低烷基基团，R2表示羟基的保护基，通过脱保护和同时环闭反应。
• Process for producing optically active y-Butyrolactone
  申请人：Takasago International Corporation

  公开号：EP1277748A1

  公开（公告）日：2003-01-22

  A novel process for producing optically active 3-hydroxy-γ-butyrolactone in a short step, which is superior economically and in efficiency and industrially suitable by using a starting material which is inexpensive and easily available and reagents easy to handle. This invention relates to a process for producing optically active 3-hydroxy-γ-butyrolactone represented by formula I: wherein the symbol * means an asymmetric carbon atom, which comprises hydrogenating an optically active 4-substituted oxy-3-hydroxybutyrate represented by formula II: wherein R1 represents a C1-4 lower alkyl group, R2 represents a protective group for a hydroxyl group deprotected by hydrogenation with a heterogeneous hydrogenation catalyst, and the symbol * has the same meaning as defined above, in the presence of a heterogeneous hydrogenation catalyst and an acidic substance followed by deprotection and simultaneous ring closure thereof.

  一种在短步骤内生产光学活性 3-羟基-γ-丁内酯的新工艺，该工艺通过使用廉价易得的起始原料和易于处理的试剂，在经济性和效率方面具有优越性，并适用于工业。本发明涉及一种生产光学活性 3-羟基-γ-丁内酯的工艺，由式 I 表示： 其中符号 * 表示不对称碳原子，该工艺包括氢化由式 II 代表的具有光学活性的 4-取代氧基-3-羟基丁酸酯： 其中 R1 代表 C1-4 低级烷基，R2 代表通过异相氢化催化剂氢化脱保护羟基的保护基团，符号 * 的含义与上述定义相同，在异相氢化催化剂和酸性物质存在下，然后脱保护并同时闭环。
• Process for producing optically active alpha butyrolactone
  申请人：Takasago International Corporation

  公开号：EP1403262A1

  公开（公告）日：2004-03-31

  A novel process for producing optically active 3-hydroxy-γ-butyrolactone in a short step, which is superior economically and in efficiency and industrially suitable by using a starting material which is inexpensive and easily available and reagents easy to handle. This invention relates to a process for producing optically active 3-hydroxy-γ-butyrolactone represented by formula I: wherein the symbol * means an asymmetric carbon atom, which comprises hydrogenating an optically active 4-substituted oxy-3-hydroxybutyrate represented by formula II: wherein R1 represents a C1-4 lower alkyl group, R2 represents a protective group for a hydroxyl group deprotected by hydrogenation with a heterogeneous hydrogenation catalyst, and the symbol * has the same meaning as defined above, in the presence of a heterogeneous hydrogenation catalyst and an acidic substance followed by deprotection and simultaneous ring closure thereof.

  一种在短步骤内生产光学活性 3-羟基-γ-丁内酯的新工艺，该工艺通过使用廉价易得的起始原料和易于处理的试剂，在经济性和效率方面具有优越性，并适用于工业。本发明涉及一种生产光学活性 3-羟基-γ-丁内酯的工艺，由式 I 表示： 其中符号 * 表示不对称碳原子，该工艺包括氢化由式 II 代表的具有光学活性的 4-取代氧基-3-羟基丁酸酯： 其中 R1 代表 C1-4 低级烷基，R2 代表通过异相氢化催化剂氢化脱保护羟基的保护基团，符号 * 的含义与上述定义相同，在异相氢化催化剂和酸性物质存在下，然后脱保护并同时闭环。
• US6608214B2
  申请人：——

  公开号：US6608214B2

  公开（公告）日：2003-08-19