methyl (2R,3R)-2-hydroxy-3-(p-methoxyphenyl)-3-(o-nitrophenylthio)propanoate | 125354-94-1

• 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: methyl (2R,3R)-2-hydroxy-3-(p-methoxyphenyl)-3-(o-nitrophenylthio)propanoate
• 英文别名: methyl (2R,3R)-2-hydroxy-3-(4-methoxyphenyl)-3-(2-nitrophenyl)sulfanylpropanoate
• CAS: 125354-94-1
• 化学式: C₁₇H₁₇NO₆S
• 分子量: 363.391
• InChiKey: FULUJKXDCQTJJV-JKSUJKDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (2R,3R)-2-hydroxy-3-(p-methoxyphenyl)-3-(o-nitrophenylthio)propanoate 生成 苯甲醇,-α--(1-氨基-2-丙烯基)-(9CI)
  参考文献：
  名称：

  INOUEH, XIROATSU;XASIYAMA, TOMIKI

  摘要：

  DOI：
• 作为产物：
  描述：

  o-nitrobenzenethiol sodium salt 在 bakers' yeast 葡萄糖 、 magnesium sulfate 、 calcium carbonate 作用下， 以 phosphate buffer 、 甲苯 为溶剂， 反应 120.0h， 生成 methyl (2R,3R)-2-hydroxy-3-(p-methoxyphenyl)-3-(o-nitrophenylthio)propanoate
  参考文献：
  名称：

  通过贝克酵母还原不对称合成 3-Hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one 的新方案

  摘要：

  报道了一种不对称合成 3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one 的新方案。茴香醛与二氯乙酸酯的 Darzens 缩合反应，随后邻硝基苯硫醇钠的取代反应和面包酵母还原提供 2-羟基-3-(4-甲氧基苯基)-3-(2-硝基苯硫基)-丙酸酯。进一步还原硝基并环化得到标题化合物。

  DOI：

  10.3987/com-05-s(k)57

文献信息

• A Lipid-Lipase Aggregate with Ether Linkage as a New Type of Immobilized Enzyme for Enantioselective Hydrolysis in Organic Solvents.
  作者：Hiroyuki AKITA、Isao UMEZAWA、Hiroko MATSUKURA、Takeshi OISHI

  DOI：10.1248/cpb.40.318

  日期：——

  For the purpose of carrying out smoothly enzymatic reaction of water-insoluble substrates in organic solvents, a new type of immobilized enzyme, a lipid-lipase aggregate, was developed. In order to prepare various kinds of lipid-lipase aggregates, 27 kinds of dialkyl ether-type phospholipid analogues were newly synthesized and used for the preparation of aggregates with lipase. Thus obtained lipid-lipase aggregates were found to catalyze the enantioselective hydrolysis of the (±)-α-acyloxy ester 2 much more efficiently than lipase immobilized with synthetic prepolymer (ENTP-4000) in water-saturated isopropyl ether. Namely. the reaction time became much shorter (2 to 3d for completion as compared with 21 d) and the chemical and optical yields of the reaction products were found to be high.

  为了顺利进行水不溶性底物在有机溶剂中的酶促反应，开发了一种新型的固定化酶——脂质-脂肪酶聚集体。为了制备各种脂质-脂肪酶聚集体，新合成了27种二烷基醚型磷脂类似物，并用于制备与脂肪酶的聚集体。所得的脂质-脂肪酶聚集体被发现能够比在水分饱和的异丙醚中通过合成预聚物（ENTP-4000）固定的脂肪酶更有效地催化（±）-α-酰氧基酯2的对映选择性水解。即，反应时间大大缩短（完成需要2至3天，而之前需要21天），并且反应产物的化学和光学产率都很高。
• Enzymatic Hydrolysis in Organic Solvents for Kinetic Resolution of Water-Insoluble .ALPHA.-Acyloxy Esters with Immobilized Lipases.
  作者：Hiroyuki AKITA、Isao UMEZAWA、Hiroko MATSUKURA

  DOI：10.1248/cpb.45.272

  日期：——

  Enantioselective hydrolysis of water-insoluble α-acyloxy esters, (±)-5 and (±)-6, was carried out using lipases immobilized with Celite or a synthetic prepolymer (ENTP-4000 or ENT-4000) in a water-saturated organic solvent to produce chiral intermediates, (2S, 3S)-5 and (2S, 3R)-4, for the synthesis of diltiazem hydrochloride 1 and (-)-indolmycin 2, respectively. Furthermore, enantioselective hydrolysis of (±)-6 using lipid-lipase aggregates in water-saturated organic solvent was also found to give (2S, 3R)-4.

  选择性水解水不溶性α-酰氧基酯(±)-5和(±)-6，采用用Celite或合成预聚合物(ENTP-4000或ENT-4000)固定化的脂肪酶，在饱和水的有机溶剂中进行，生成用于合成盐酸地尔尼定1和(-)-吲哚霉素2的手性中间体(2S, 3S)-5和(2S, 3R)-4。此外，使用脂质-脂肪酶聚集体在饱和水的有机溶剂中对(±)-6进行选择性水解同样得到了(2S, 3R)-4。
• A lipid-lipase aggregate as a new type of immobilized enzyme.
  作者：Hiroyuki AKITA、Isao UMEZAWA、Hiroko MATSUKURA、Takeshi OISHI

  DOI：10.1248/cpb.39.1632

  日期：——

  Lipid-lipase aggregate was prepared by mixing an aqueous solution of lipase with a benzene solution of synthetic phospholipids. The precipitated solid aggregate catalyzed effectively an asymmetric hydrolysis of water-insoluble (±)-α-acyloxy ester 2__∼ in water-saturated isopropy ether producing (2S, 3S)-2__∼, a key intermediate for the medicinally active diltiazem hydrochloride 1__∼.

  通过将脂肪酶水溶液与合成磷脂的苯溶液混合，制备出了脂质-脂肪酶聚合体。沉淀的固体聚合体在水饱和异丙醚中有效地催化了不溶于水的（±）-α-乙酰氧基酯 2__∼ 的不对称水解，生成了 (2S，3S)-2__∼，这是具有药用活性的盐酸地尔硫卓 1__∼ 的关键中间体。
• Structural Characteristics of Lipid-Lipase Aggregates for Enantioselective Hydrolysis in Organic Solvents.
  作者：Hiroyuki AKITA、Isao UMEZAWA、Ikuko SAKURAI、Takeshi OISHI

  DOI：10.1248/cpb.41.12

  日期：——

  An ether-linked lipid-lipase aggregate was found to function as an immobilized biocatalyst. Three kinds of aggregate, I, III, and IV, obtained by sonication treatment were considered to have stacked bilayer structure of the lipid in the crystalline phase based on X-ray diffraction analysis. On the other hand, aggregate II obtained by the stirring method appeared to have an inverted micellar structure.

  研究发现，一种醚键脂质-脂肪酶聚合体可作为固定化生物催化剂发挥作用。根据 X 射线衍射分析，通过超声处理获得的 I、III 和 IV 三种聚合体在结晶相中具有脂质的叠层双分子结构。另一方面，搅拌法得到的聚合体 II 似乎具有倒胶束结构。
• Akita, Hiroyuki; Enoki, Yuko; Yamada, Harutami, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 10, p. 2876 - 2878
  作者：Akita, Hiroyuki、Enoki, Yuko、Yamada, Harutami、Oishi, Takeshi

  DOI：——

  日期：——