2-[(4S)-2-ethyl-5-oxo-1,3-dioxolan-4-yl]acetic acid | 1170702-13-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-[(4S)-2-ethyl-5-oxo-1,3-dioxolan-4-yl]acetic acid
• 英文别名: (4S)-2-Ethyl-5-oxo-1,3-dioxolane-4-acetic acid
• CAS: 1170702-13-2
• 化学式: C₇H₁₀O₅
• 分子量: 174.153
• InChiKey: VBWHZEYYJTZAMI-VKZKZBKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  2-[(4S)-2-ethyl-5-oxo-1,3-dioxolan-4-yl]acetic acid 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 cis-2-[(4S)-2-ethyl-5-oxo-1,3-dioxolan-4-yl]ethanol 、 trans-2-[(4S)-2-ethyl-5-oxo-1,3-dioxolan-4-yl]ethanol
  参考文献：
  名称：

  (+)-Brasilenyne 的全合成。分子内硅辅助交叉偶联反应的应用

  摘要：

  (+)-brasilenyne (1) 的第一个对映选择性全合成已在 19 个线性步骤中实现，1-(S)-苹果酸的总产率为 5.1%。包含 1,3-cis,cis 二烯单元的 oxonin 核心的构建是通过串联闭环复分解/硅辅助分子内交叉偶联反应完成的。此外，一个关键的炔丙基立体中心是通过由 TiCl(4) 促进的 1,3-二氧戊环的新型、高度非对映选择性环开口创建的。该反应通过氧代碳正离子中间体进行，不对称诱导完全由 l-苹果酸残基控制。C(8) 立体中心由试剂控制的不对称烯丙基硼化设置。

  DOI：

  10.1021/ja0466863
• 作为产物：
  描述：

  L-苹果酸 、 丙醛 在 三氟化硼乙醚 作用下， 以 乙醚 为溶剂， 反应 3.5h， 以78.1%的产率得到2-[(4S)-2-ethyl-5-oxo-1,3-dioxolan-4-yl]acetic acid
  参考文献：
  名称：

  EP2230239

  摘要：

  公开号：

文献信息

• A METHOD FOR PREPARING 4-Ý9-(6-AMINOPURINE)¨-2-(S)-HYDROXYL-BUTYRIC ACID METHYL ESTER
  申请人：SHANGHAI INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF SCIENCES

  公开号：EP2230239A1

  公开（公告）日：2010-09-22

  The present invention discloses a novel method for preparing and purifying 4-(6-Amino-purin-9-yl)-2(S)-hydroxy-butyric acid methyl ester. The preparation started from cheap and easily available L-malic acid, which was transformed to intermediate I after simultaneous protection of the groups of 1-carboxyl and 2-hydroxyl. The intermediate I was selectively reduced to intermediate alcohol II, whose hydroxyl group was further transformed to an easily leaving group to afford intermediate III. The intermediate III was nucleophilically substituted with adenine to afford intermediate IV The intermediate IV was deprotected and methyl-esterified simultaneously in methanol in the presence of an acid or a base to afford crude 4-(6-Amino-purin-9-yl)-2(S)-hydroxy-butyric acid methyl ester, which was purified by recrystallization to afford the purified product. Comparing with the prior preparation methods, the present method has advantages in low cost, mild conditions, high retention of the chiral center during the reaction, high productivity, great improvement in the quality and yield of the product and great decrease in cost, and thus is suitable for the production on a large scale.

  本发明公开了一种制备和纯化 4-(6-氨基-嘌呤-9-基)-2(S)-羟基丁酸甲酯的新方法。该制备方法从廉价易得的 L-苹果酸开始，在同时保护 1-羧基和 2-羟基后将其转化为中间体 I。中间体 I 被选择性地还原成中间体醇 II，其羟基进一步转化为易离去基团，得到中间体 III。中间体 IV 在甲醇中，在酸或碱的存在下同时进行脱保护和甲基酯化，得到粗制的 4-(6-氨基-嘌呤-9-基)-2(S)-羟基丁酸甲酯。与之前的制备方法相比，本方法具有成本低、条件温和、反应过程中手性中心保留率高、生产率高、产品质量和收率大大提高、成本大大降低等优点，适合大规模生产。
• Method for Preparing 4-[9-(6-Aminopurine)]-2-(S)-Hydroxyl-Butyric Acid Methyl Ester
  申请人：Nan Fajun

  公开号：US20110201810A1

  公开（公告）日：2011-08-18

  The present invention discloses a novel method for preparing and purifying 4-(6-Amino-purin-9-yl)-2(S)-hydroxy-butyric acid methyl ester. The preparation started from cheap and easily available L-malic acid, which was transformed to intermediate I after simultaneous protection of the groups of 1-carboxyl and 2-hydroxyl. The intermediate I was selectively reduced to intermediate alcohol II, whose hydroxyl group was further transformed to an easily leaving group to afford intermediate III. The intermediate III was nucleophilically substituted with adenine to afford intermediate IV. The intermediate IV was deprotected and methyl-esterified simultaneously in methanol in the presence of an acid or a base to afford crude 4-(6-Amino-purin-9-yl)-2(S)-hydroxy-butyric acid methyl ester, which was purified by recrystallization to afford the purified product. Comparing with the prior preparation methods, the present method has advantages in low cost, mild conditions, high retention of the chiral center during the reaction, high productivity, great improvement in the quality and yield of the product and great decrease in cost, and thus is suitable for the production on a large scale.
• US8247549B2
  申请人：——

  公开号：US8247549B2

  公开（公告）日：2012-08-21
• EP2230239
  申请人：——

  公开号：——

  公开（公告）日：——
• Total Synthesis of (+)-Brasilenyne. Application of an Intramolecular Silicon-Assisted Cross-Coupling Reaction
  作者：Scott E. Denmark、Shyh-Ming Yang

  DOI：10.1021/ja0466863

  日期：2004.10.1

  3-cis,cis diene unit was accomplished with a tandem ring-closing metathesis/silicon-assisted intramolecular cross-coupling reaction. In addition, a key propargylic stereogenic center was created through a novel, highly diastereoselective ring opening of a 1,3-dioxolanone promoted by TiCl(4). This reaction proceeded through an oxocarbenium ion intermediate and the asymmetric induction was fully controlled

  (+)-brasilenyne (1) 的第一个对映选择性全合成已在 19 个线性步骤中实现，1-(S)-苹果酸的总产率为 5.1%。包含 1,3-cis,cis 二烯单元的 oxonin 核心的构建是通过串联闭环复分解/硅辅助分子内交叉偶联反应完成的。此外，一个关键的炔丙基立体中心是通过由 TiCl(4) 促进的 1,3-二氧戊环的新型、高度非对映选择性环开口创建的。该反应通过氧代碳正离子中间体进行，不对称诱导完全由 l-苹果酸残基控制。C(8) 立体中心由试剂控制的不对称烯丙基硼化设置。