ethyl (S)-3-(methoxymethoxy)butanoate | 73267-69-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (S)-3-(methoxymethoxy)butanoate
• 英文别名: ethyl (3S)-3-(methoxymethoxy)butanoate
• CAS: 73267-69-3
• 化学式: C₈H₁₆O₄
• 分子量: 176.213
• InChiKey: UVGZBMQFZVSKNQ-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (S)-3-(methoxymethoxy)butanoate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以85%的产率得到(S)-3-(methoxymethoxy)-1-butanol
  参考文献：
  名称：

  Studies directed toward the total synthesis of streptogramin antibiotics. Enantiospecific approach to the nine-membered macrocycle of griseoviridin

  摘要：

  DOI：

  10.1021/ja00522a085
• 作为产物：
  描述：

  3-羟基丁酸乙酯 、 氯甲基甲基醚 在 N,N-二乙基苯胺 作用下， 反应 72.0h， 以89%的产率得到ethyl (S)-3-(methoxymethoxy)butanoate
  参考文献：
  名称：

  Studies directed toward the total synthesis of streptogramin antibiotics. Enantiospecific approach to the nine-membered macrocycle of griseoviridin

  摘要：

  DOI：

  10.1021/ja00522a085

文献信息

• A Novel Route to the Vinyl Sulfide Nine-Membered Macrocycle Moiety of Griseoviridin^†
  作者：Enrico Marcantoni、Massimo Massaccesi、Marino Petrini、Giuseppe Bartoli、Maria Cristina Bellucci、Marcella Bosco、Letizia Sambri

  DOI：10.1021/jo000116d

  日期：2000.7.1

  The synthetic potentialities of cerium(III) chloride are demonstrated by the synthesis of a nine-membered ring heterocycle component of Griseoviridin (3) in optically active form. The key step involves the stereospecific formation of the alpha-carbalkoxy alkenyl sulfide moiety using a combination system of cerium(III) chloride heptahydrate and sodium iodide.

  氯化铈（III）的合成潜力已通过光学活性形式的Griseoviridin（3）的九元环杂环成分的合成得到证明。关键步骤涉及使用七水合氯化铈（III）和碘化钠的组合系统立体定向形成α-烷氧基氧基烯基硫醚部分。
• Approaches toward the Total Synthesis of the Nine-Membered Thio-Lactone Core of Griseoviridin
  作者：Xavier Moreau、Jean-Marc Campagne

  DOI：10.1021/jo034195f

  日期：2003.6.1

  toward the synthesis of the macrocyclic thiolactone core of griseoviridin have been studied. Intramolecular palladium-catalyzed thiol coupling and esterification (carboxylate activation) have led to the formation of unexpected rearranged products. An intermolecular palladium-catalyzed thiol/vinyl iodide coupling followed by an esterification (alcohol activation) ultimately led to the nine-membered

  已经研究了三种合成灰黄绿异丁烯的大环硫代内酯核心的方法。分子内钯催化的硫醇偶联和酯化（羧酸酯活化）导致形成意想不到的重排产物。分子间钯催化的硫醇/碘化乙烯偶联，然后进行酯化（酒精活化），最终导致灰黄霉素的九元核心。
• Kinetic resolution of poly(ethylene glycol)-supported carbonates by enzymatic hydrolysis
  作者：Masaki Nogawa、Megumi Shimojo、Kazutsugu Matsumoto、Masayuki Okudomi、Yuji Nemoto、Hiromichi Ohta

  DOI：10.1016/j.tet.2006.05.020

  日期：2006.7

  The enzyme-mediated enantioselective hydrolysis of poly(ethylene glycol) (PEG)-supported carbonates is disclosed. The water-soluble carbonates were prepared by immobilization of a racemic secondary alcohol (4-benzyloxy-2-butanol) onto low-molecular weight (av MW 550 and 750) monometboxy PEG through a carbonate linker. For the screening of the hydrolytic enzymes, the substrate was enantioselectively hydrolyzed by commercially available lipase from porcine pancreas (PPL; Type II, Sigma) to afford the optically active compounds. In this system, the separation of the remaining (S)-substrate and the resulting (R)-alcohol was achieved by an extraction process without a laborious column chromatography. The (S)-carbonate was easily hydrolyzed with K2CO3 to afford the corresponding (S)-alcohol. Other MPEG-supported substrates were also hydrolyzed to afford the corresponding optically active alcohols. (c) 2006 Elsevier Ltd. All rights reserved.