methyl 10-((tert-butyldimethylsilyl)oxy)decanoate | 226243-93-2

• 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: methyl 10-((tert-butyldimethylsilyl)oxy)decanoate
• 英文别名: Methyl 10-[tert-butyl(dimethyl)silyl]oxydecanoate；methyl 10-[tert-butyl(dimethyl)silyl]oxydecanoate
• CAS: 226243-93-2
• 化学式: C₁₇H₃₆O₃Si
• 分子量: 316.557
• InChiKey: SRQWDLBQGQTPDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21.0
• 可旋转键数：
  11.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 10-((tert-butyldimethylsilyl)oxy)decanoate 在 四氯化钛 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 3.58h， 生成
  参考文献：
  名称：

  [EN] METHOD FOR PRODUCING IONIZABLE LIPIDS OR INTERMEDIATES FOR THE SYNTHESIS OF SUCH LIPIDS
  [FR] PROCÉDÉ DE PRODUCTION DE LIPIDES IONISABLES OU D'INTERMÉDIAIRES POUR LA SYNTHÈSE DE TELS LIPIDES

  摘要：

  The present disclosure provides a method for producing one or more intermediates for the synthesis of one or more ionizable lipids, the method comprising: (i) producing a beta-ketoacid by reacting a cyclic ester, a terminal hydroxy ester or a derivative thereof, a dicarboxylic acid half ester, or an acid chloride derivative of the dicarboxylic acid half ester, in a condensation reaction, thereby producing the beta-ketoacid or a beta-ketoester that is hydrolyzed to produce the beta-ketoacid and (ii) decarboxylating the beta-ketoacid, thereby producing the one or more intermediates, wherein the one or more intermediates have a structure that may be defined by Formula A. Further provided is a method for producing an ionizable lipid from the intermediate comprising adding an ionizable head group moiety to (a) a ketone group of one or more intermediates having the structure that may be defined by Formula A; or (b) a corresponding alcohol of the intermediate.

  公开号：

  WO2023147657A1
• 作为产物：
  描述：

  癸二酸单甲酯 在 咪唑 、 dimethyl sulfide borane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 19.5h， 生成 methyl 10-((tert-butyldimethylsilyl)oxy)decanoate
  参考文献：
  名称：

  [EN] METHOD FOR PRODUCING IONIZABLE LIPIDS OR INTERMEDIATES FOR THE SYNTHESIS OF SUCH LIPIDS
  [FR] PROCÉDÉ DE PRODUCTION DE LIPIDES IONISABLES OU D'INTERMÉDIAIRES POUR LA SYNTHÈSE DE TELS LIPIDES

  摘要：

  The present disclosure provides a method for producing one or more intermediates for the synthesis of one or more ionizable lipids, the method comprising: (i) producing a beta-ketoacid by reacting a cyclic ester, a terminal hydroxy ester or a derivative thereof, a dicarboxylic acid half ester, or an acid chloride derivative of the dicarboxylic acid half ester, in a condensation reaction, thereby producing the beta-ketoacid or a beta-ketoester that is hydrolyzed to produce the beta-ketoacid and (ii) decarboxylating the beta-ketoacid, thereby producing the one or more intermediates, wherein the one or more intermediates have a structure that may be defined by Formula A. Further provided is a method for producing an ionizable lipid from the intermediate comprising adding an ionizable head group moiety to (a) a ketone group of one or more intermediates having the structure that may be defined by Formula A; or (b) a corresponding alcohol of the intermediate.

  公开号：

  WO2023147657A1

文献信息

• Synthesis of racemic 9-methyl-10-hexadecenoic acid
  作者：Néstor M. Carballeira、Anthony Sostre、José A. Restituyo

  DOI：10.1016/s0009-3084(98)00101-7

  日期：1999.2

  The marine bacterial fatty acid 9-methyl-10-hexadecenoic acid was conveniently prepared in 6 steps and in a 22% overall yield, starting from commercially available methyl 10-hydroxydecanoate. The naturally occurring fatty acid has the E double bond configuration as confirmed by gas chromatographic co-elution experiments.

  从市售的10-羟基癸酸甲酯开始，以6个步骤方便地以22％的总产率制备海洋细菌脂肪酸9-甲基-10-十六碳烯酸。如气相色谱共洗脱实验所证实，天然存在的脂肪酸具有E双键构型。