tert-butyl 3-oxo-5-hydroxy-6-benzyloxyhexanoate | 312745-89-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl 3-oxo-5-hydroxy-6-benzyloxyhexanoate
• 英文别名: (5S)-6-benzyloxy-5-hydroxy-3-oxohexanoic tert-butyl ester；Tert-butyl 6-benzyloxy-5-hydroxy-3-oxohexanoate；Tert-butyl 5-hydroxy-3-oxo-6-phenylmethoxyhexanoate
• CAS: 312745-89-4
• 化学式: C₁₇H₂₄O₅
• 分子量: 308.375
• InChiKey: VBXDDEFKXNFJLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-oxo-5-hydroxy-6-benzyloxyhexanoate 在 platinum on carbon 氢气 、 双氧水 、 magnesium acetate 作用下， 以 甲醇 为溶剂， 20.0~25.0 ℃ 、2.0 MPa 条件下， 反应 3.0h， 生成 tert-butyl (3R,5S)-6-(benzyloxy)-3,5-dihydroxyhexanoate 、 (3R,5R)-6-benzyloxy-3,5-dihydroxy-hexanoic acid tert-butyl ester
  参考文献：
  名称：

  Diastereoselective hydrogenation of 1,3-hydroxyketones

  摘要：

  这项发明涉及一种新型的对1,3-羟基酮进行不对映选择性加氢的方法，其化学式为(I)，其中R、R'和R''如权利要求1所定义，在溶剂中，在存在镁盐、非均相铂催化剂和可选氧化剂的情况下进行。

  公开号：

  US20040010154A1
• 作为产物：
  描述：

  醋酸叔丁酯 、 ethyl 4-(benzyloxy)-3-hydroxybutanoate 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 16.5h， 以55%的产率得到tert-butyl 3-oxo-5-hydroxy-6-benzyloxyhexanoate
  参考文献：
  名称：

  Processes for the preparation of 5-hydroxy-3-oxopentanoic acid derivatives

  摘要：

  这项发明提供了一种从易得、廉价的起始材料中轻松生产一种有用的药物中间体5-羟基-3-氧代戊酸的方法，而无需使用任何特殊的生产设备，如极低温反应器。因此，这项发明提供了一种生产5-羟基-3-氧代戊酸的方法，包括让锂酰胺作用于乙酸酯和3-羟基丙酸衍生物的混合物，温度不低于-20°C。此外，这项发明还提供了一种生产5-羟基-3-氧代戊酸的方法，包括用格氏试剂处理乙酸酯和3-羟基丙酸衍生物的混合物，以制备上述结构式(I)的化合物和乙酸酯的混合物，然后让锂酰胺在不低于-20°C的温度下作用于该混合物。

  公开号：

  US06340767B1

文献信息

• PROCESSES FOR THE PREPARATION OF 5-HYDROXY-3-OXOPENTANOIC ACID DERIVATIVES
  申请人：KANEKA CORPORATION

  公开号：EP1104750A1

  公开（公告）日：2001-06-06

  Processes by which 5-hydroxy-3-oxopentanoic acid derivatives useful as intermediates of drugs can be prepared from inexpensive and easily available raw materials under noncryogenic conditions. Specifically, a process for preparing 5-hydroxy-3-oxopentanoic acid derivatives by making lithium amide act on a mixture of an acetic acid ester and a 3-hydroxypropionic acid derivative at a temperature of -20 °C or above; and another process for preparing 5-hydroxy-3-oxopentanoic acid derivatives by treating a mixture of an acetic acid ester and a 3-hydroxypropionic acid derivative with a Grignard reagent and then making lithium amide act on the resulting mixture at a temperature of -20 °C or above.

  在非致冷条件下，用廉价易得的原料制备可用作药物中间体的 5-羟基-3-氧代戊酸衍生物的工艺。具体来说，一种制备 5-羟基-3-氧代戊酸衍生物的工艺是在-20℃或以上的温度下使锂酰胺作用于乙酸酯和 3-羟基丙酸衍生物的混合物；以及另一种制备 5-羟基-3-氧代戊酸衍生物的工艺，其方法是用格氏试剂处理乙酸酯和 3-羟基丙酸衍生物的混合物，然后在-20℃或以上的温度下使锂酰胺作用于生成的混合物。
• Synthesis of ethyl and t-butyl (3R,5S)-dihydroxy-6-benzyloxy hexanoates via diastereo- and enantioselective microbial reduction
  作者：Zhiwei Guo、Yijun Chen、Animesh Goswami、Ronald L. Hanson、Ramesh N. Patel

  DOI：10.1016/j.tetasy.2006.05.027

  日期：2006.6

  Previously we have demonstrated the reduction of ethyl diketoester 4 to the corresponding dihydroxy ester 6a by Acinetobacter sp. SC13874. Recently we screened more than 100 cultures for microbial reduction of both the ethyl and t-butyl diketoesters 4 and 5. Most yeast cultures showed a preference for reduction at the C-3 with low enantioselectivity. Among the three Acinetobacter strains screened, Acinetobacter sp. SC13874 reduced both compounds 4 and 5 to the corresponding (3R)- and (5S)-monohydroxy compounds. Monohydroxy compounds were isolated and their absolute configurations determined. (3R)- and (5S)-Monohydroxy compounds were reduced further to the corresponding dihydroxy esters 6a and 8a to provide alternate routes for the synthesis of compounds 14a nd 16a, potential intermediates for the synthesis of HMG-CoA reductase inhibitors. Cell suspensions of Acinetobacter sp. SC13874 reduced the ethyl diketoester 4 to a mixture of desired syn and undesired anti diastereomers. The desired syn-(3R,5S)-dihydroxy ester 6a was obtained with an enantiomeric excess (ee) of 99% and a diastereomeric excess (de) of 63%. Cell suspensions reduced the t-butyl diketoester 5 to a mixture of mono- and dihydroxy esters with the dihydroxy ester showing an ee of 87% and de of 51% for the desired syn(3R,5S)-dihydroxy ester 8a. Three different ketoreductases were purified to homogeneity, and their biochemical properties compared. Reductase I only catalyzes the reduction of ethyl diketoester 4 to its monohydroxy products 10 and 11, whereas reductase II catalyzes the formation of dihydroxy products 6 and 7 from monohydroxy substrates 10 and 11. A third reductase (III) was identified, which catalyzes the reduction of diketoester 4 to syn-(3R,5S)-dihydroxy ester 6a. (c) 2006 Elsevier Ltd. All rights reserved.
• US6340767B1
  申请人：——

  公开号：US6340767B1

  公开（公告）日：2002-01-22
• USRE39333E1
  申请人：——

  公开号：USRE39333E1

  公开（公告）日：2006-10-10
• Diastereoselective hydrogenation of 1,3-hydroxyketones
  申请人：——

  公开号：US20040010154A1

  公开（公告）日：2004-01-15

  The invention relates to a novel process of diastereoselective hydrogenation of 1,3-hydroxyketones of formula (I) 1 wherein R, R′ and R″ are as defined in claim 1 which is carried out in a solvent in the presence of a magnesium salt, a heterogeneous platinum catalyst and optionally an oxidant.

  这项发明涉及一种新型的对1,3-羟基酮进行不对映选择性加氢的方法，其化学式为(I)，其中R、R'和R''如权利要求1所定义，在溶剂中，在存在镁盐、非均相铂催化剂和可选氧化剂的情况下进行。