(S)-6-benzoyloxy-3-oxo-5-hydroxyhexanoic acid tert-butylester | 131690-27-2

• 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: (S)-6-benzoyloxy-3-oxo-5-hydroxyhexanoic acid tert-butylester
• 英文别名: (5S)-6-benzoyloxy-5-hydroxy-3-oxohexanoic acid tert-butyl ester；tert.-butyl 5S-hydroxy-6-benzoyloxy-3-oxohexanoate；[(2S)-2-hydroxy-6-[(2-methylpropan-2-yl)oxy]-4,6-dioxohexyl] benzoate
• CAS: 131690-27-2
• 化学式: C₁₇H₂₂O₆
• 分子量: 322.358
• InChiKey: LXNMDVIPWIOXIE-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-6-benzoyloxy-3-oxo-5-hydroxyhexanoic acid tert-butylester 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 (5S)-6-benzoyloxy-3,5-dihydroxyhexanoic tert-butyl ester
  参考文献：
  名称：

  Process for the production of 3,5,6-trihydroxyhexanoic acid derivative

  摘要：

  一种化合物，其为3,5,6-三羟基己酸衍生物，化学式如下：##STR1## 其中P1和P2分别是氢原子或羟基保护基，或者一起形成一个环，R为烷基基团，通过以下步骤有效制备：将以下化学式的丁腈衍生物：##STR2## 其中P1和P2的定义与上述相同，与以下化学式的α-卤代乙酸酯：X--CH2--COOR (III) 反应，其中X为卤素原子，R的定义与上述相同，在选择自锌和锌-铜组成的金属催化剂存在下，形成以下酮酸衍生物：##STR3## 其中P1、P2和R的定义与上述相同，然后还原得到的酮酸衍生物（IV）。

  公开号：

  US04983759A1
• 作为产物：
  描述：

  tert-butyl 2-[(4S)-2,4-dihydroxyoxolan-2-yl]acetate 、 苯甲酰氯 在 吡啶 作用下， 以74%的产率得到(S)-6-benzoyloxy-3-oxo-5-hydroxyhexanoic acid tert-butylester
  参考文献：
  名称：

  Efficient Synthesis of (3R,5S)-3,5,6-Trihydroxyhexanoic Acid Derivative as a Chiral Side Chain of Statins

  摘要：

  Efficient synthesis of tert-butyl [(3R,5S)-6-hydroxymeth yl-2,2-dimethyl-1,3-dioxan-4-yl]acetate (1) has been accomplished. Unprecedented hydration of 3 in the presence of lithium chloride provided 4a,b, the primary hydroxyl group of which reacted with pivaloyl-and I-naphthoyl chloride, respectively, in pyridine to give 7a or 7d in improved selectivity. Diastereoselective reduction of 7a and protection-deprotection sequence provided 1.

  DOI：

  10.1055/s-2008-1078428

文献信息

• Process for preparing optically active 2-[6-(hydroxy-methyl)-1,3-dioxan-4-yl] acetic acid derivatives
  申请人：Nishiyama Akira

  公开号：US20050080277A1

  公开（公告）日：2005-04-14

  The present invention is to provide a production technology by which an optically active 2-[6-(hydroxymethyl)-1,3-dioxan-4-yl]acetic acid derivative, which are of value as pharmaceutical intermediates, can be produced from inexpensive and readily available starting materials without using any extraordinary equipment such as an ultra-low-temperature reactor. The present invention is a production process of an optically active 2-[6-(hydroxymethyl)-1,3-dioxan-4-yl]acetic acid derivative which comprises reacting an enolate, prepared by permitting a base or a 0-valent metal to act on an acetic acid ester derivative with (S)-β-hydroxy-γ-butyrolactone at a temperature not lower than −30° C. to give a dihydroxyoxohexanoic acid derivative, treating the same with an acylating agent in the presence of a base to produce a dihydroxyoxohexanoic acid monoacyl derivative, reducing this compound with a microorganism to produce a trihydroxyhexanoic acid monoacyl derivative, treating this compound with an acetal-forming reagent in the presence of an acid catalyst to produce an acyloxymethyldioxanylacetic acid derivative, and finally, subjecting this compound to solvolysis in the presence of a base.

  本发明旨在提供一种生产技术，通过该技术可以从廉价且易得的起始材料中生产出具有药物中间体价值的光学活性2-[6-(羟甲基)-1,3-二氧杂环戊-4-基]乙酸衍生物，而无需使用任何特殊设备，如超低温反应器。本发明是一种光学活性2-[6-(羟甲基)-1,3-二氧杂环戊-4-基]乙酸衍生物的生产过程，包括将碱或0价金属作用于乙酸酯衍生物制备出的烯醇，与(S)-β-羟基-γ-丁内酯在不低于-30℃的温度下反应，得到二羟基氧代己酸衍生物，用酰化剂在碱的存在下处理，以产生二羟基氧代己酸单酰衍生物，用微生物还原该化合物以产生三羟基己酸单酰衍生物，用酸催化剂存在下的缩醛试剂处理该化合物，以产生酰氧甲基二氧杂环己酸衍生物，最后，在碱的存在下进行溶剂解离。
• Process for producing optically active 3,5-dihydroxycarboxylic acid derivative
  申请人：——

  公开号：US20040254392A1

  公开（公告）日：2004-12-16

  A method for producing an optically active 3,5-dihydroxyhexanoic acid derivative by stereoselectively reducing an optically active 3-oxo-5-hydroxyhexanoic acid derivative is provided. The method, which requires neither an ultralow-temperature reactor, an incubator, nor protection of the 5-position hydroxy group, is simple and economical. An optically active 3,5-dihydroxyhexanoic acid derivative is produced by asymmetrical hydrogenation of an optically active 3-oxo-5-hydroxyhexanoic acid derivative catalyzed by an RuBr 2 BINAP complex prepared from a ruthenium complex and a ruthenium-optically active phosphine complex, i.e., 2,2′-bisdiarylphosphino-1,1′-binaphthyl (BINAP), while using extremely inexpensive hydrogen as the reductant.

  提供了一种通过立体选择性还原光学活性3-氧代-5-羟基己酸衍生物来制备光学活性3,5-二羟基己酸衍生物的方法。该方法既不需要超低温反应器、孵化器，也不需要保护5-位羟基，简单经济。通过使用一种由钌配合物和钌光学活性膦配合物即2,2'-双芳基膦基-1,1'-联萘（BINAP）制备的RuBr2BINAP复合物作为催化剂，使用极为廉价的氢作为还原剂，对光学活性3-氧代-5-羟基己酸衍生物进行不对称加氢，从而制备出光学活性的3,5-二羟基己酸衍生物。
• Novel Carbonyl Reductase, Gene Therefor and Use Thereof
  申请人：Kizaki Noriyuki

  公开号：US20090029430A1

  公开（公告）日：2009-01-29

  The present invention is to provide a process for efficiently producing an optically active alcohol including (R)-3-hydroxy-3-phenylpropanenitrile. One of the features of the present invention is a polypeptide having an activity of asymmetrically reducing 3-oxo-3-phenylpropanenitrile isolated from a microorganism belonging to the genus Candida to produce (R)-3-hydroxy-3-phenylpropanenitrile, DNA encoding the polypeptide and a transformant of producing the polypeptide. Another feature of the present invention is a process for producing an optically active alcohol such as (R)-3-hydroxy-3-phenylpropanenitrile by reducing a carbonyl compound such as 3-oxo-3-phenylpropanenitrile by use of the polypeptide or the transformant.

  本发明提供了一种高效生产光学活性醇的方法，包括(R)-3-羟基-3-苯基丙腈。本发明的一个特点是从属于候选属微生物中分离出具有不对称还原3-氧代-3-苯基丙腈活性的多肽，用于生产(R)-3-羟基-3-苯基丙腈，以及编码该多肽的DNA和生产该多肽的转化菌株。本发明的另一个特点是通过使用该多肽或转化菌株还原羰基化合物如3-氧代-3-苯基丙腈来生产(R)-3-羟基-3-苯基丙腈等光学活性醇的方法。
• Carbonyl reductase, gene therefor and use thereof
  申请人：Kaneka Corporation

  公开号：US08008461B2

  公开（公告）日：2011-08-30

  The present invention is to provide a process for efficiently producing an optically active alcohol including (R)-3-hydroxy-3-phenylpropanenitrile. One of the features of the present invention is a polypeptide having an activity of asymmetrically reducing 3-oxo-3-phenylpropanenitrile isolated from a microorganism belonging to the genus Candida to produce (R)-3-hydroxy-3-phenylpropanenitrile, DNA encoding the polypeptide and a transformant of producing the polypeptide. Another feature of the present invention is a process for producing an optically active alcohol such as (R)-3-hydroxy-3-phenylpropanenitrile by reducing a carbonyl compound such as 3-oxo-3-phenylpropanenitrile by use of the polypeptide or the transformant.

  本发明旨在提供一种有效生产包括(R)-3-羟基-3-苯基丙腈的光学活性醇的方法。本发明的特点之一是从属于念珠菌属的微生物中分离出具有不对称还原3-氧代-3-苯基丙腈活性的多肽，用于生产(R)-3-羟基-3-苯基丙腈，以及编码该多肽的DNA和生产该多肽的转化体。本发明的另一个特点是通过使用该多肽或转化体还原羰基化合物，如3-氧代-3-苯基丙腈，来生产光学活性醇，如(R)-3-羟基-3-苯基丙腈的方法。
• NOVEL CARBONYL REDUCTASE, GENE THEREFOR AND USE THEREOF
  申请人：KIZAKI Noriyuki

  公开号：US20130149769A1

  公开（公告）日：2013-06-13

  The present invention is to provide a process for efficiently producing an optically active alcohol including (R)-3-hydroxy-3-phenylpropanenitrile. One of the features of the present invention is a polypeptide having an activity of asymmetrically reducing 3-oxo-3-phenylpropanenitrile isolated from a microorganism belonging to the genus Candida to product (R)-3-hydroxy-3-phenylpropanenitrile, DNA encoding the polypeptide and a transformant of producing the polypeptide. Another feature of the present invention is a process for producing an optically active alcohol such as (R)-3-hydroxy-3-phenylpropanenitrile by reducing a carbonyl compound such as 3-oxo-3-phenylpropanenitrile by use of the polypeptide or the transformant.

  本发明旨在提供一种高效生产包括(R)-3-羟基-3-苯基丙腈的光学活性醇的过程。本发明的特点之一是从属于Candida属微生物中分离出具有不对称还原3-氧代-3-苯基丙腈活性的多肽，该多肽可产生(R)-3-羟基-3-苯基丙腈，编码该多肽的DNA以及产生该多肽的转化体。本发明的另一个特点是通过使用该多肽或转化体还原3-氧代-3-苯基丙腈等羰基化合物来生产光学活性醇，例如(R)-3-羟基-3-苯基丙腈。