Ethyl (2S,3R)-4-hydroxy-2,3-epoxybutyrate | 136060-81-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: Ethyl (2S,3R)-4-hydroxy-2,3-epoxybutyrate
• 英文别名: Methyl 4-hydroxy-2(S),3(R)-epoxybutyrate；methyl (2S,3R)-4-hydroxy-2,3-epoxybutyrate；methyl (2S,3R)-3-(hydroxymethyl)oxirane-2-carboxylate
• CAS: 136060-81-6
• 化学式: C₅H₈O₄
• 分子量: 132.116
• InChiKey: ICZOOULEQOMDKH-DMTCNVIQSA-N

物化性质

• 沸点：
  193.9±15.0 °C(Predicted)
• 密度：
  1.314±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl (2S,3R)-4-hydroxy-2,3-epoxybutyrate 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 sodium azide 、 四丁基氟化铵 、 sodium hexamethyldisilazane 、 氯化铵 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 Methyl (2R,3S)-1-(tert-butyloxycarbonyl)-3-<1-(3-cyanoindolyl)methyl>aziridine-2-carboxylate
  参考文献：
  名称：

  Cyclization of Chiral Carbon-Centered Aziridinyl Radicals: A New Route to Azirino[2',3':3,4]pyrrolo[1,2-a]indoles

  摘要：

  A carbon-centered aziridinyl radical has been generated from the ester of chiral aziridine carboxylic acid 5b. The resultant radical has been cyclized directly and has been brominated with CBrCl3. The bromo aziridines have also been cyclized reductively in the presence of n-Bu(3)SnH. Dihydroindole 8b bears the same relative and absolute stereochemistry as the mitomycin C nucleus.

  DOI：

  10.1021/jo00105a009
• 作为产物：
  描述：

  对甲苯磺酰氯 、 (3R,4R)-(-)-D-赤酮酸内酯 在 silica gel sodium methylate 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 为溶剂， 以1.41 g (63%)的产率得到Ethyl (2S,3R)-4-hydroxy-2,3-epoxybutyrate
  参考文献：
  名称：

  Process and intermediates for chiral epoxides

  摘要：

  手性环氧丁酸酯是通过基于催化的醇解法，从新型的二氢-3R-取代磺酰氧基-4R-羟基-2-(3H)呋喃酮高产率制备而成。所得的手性环氧丁酸酯是合成1-羰基-1-脱硫头孢菌素类抗生素的有用中间体。

  公开号：

  US05097049A1

文献信息

• Synthesis of a Versatile (<i>S</i>)-3-(Hydroxymethyl)butane-1,2,4-triol Building Block and its Application for the Stereoselective Synthesis of <i>N</i>-Homoceramides
  作者：Ulrik Hillaert、Serge Van Calenbergh

  DOI：10.1021/ol052335x

  日期：2005.12.1

  [structures: see text] A versatile (S)-3-(hydroxymethyl)butane-1,2,4-triol building block has been synthesized starting from D-isoascorbic acid, a common food preservative. The key transformation in this approach was the introduction of branching through a high yield and fully regioselective epoxide opening. This flexible synthon has been elaborated to a new class of (dihydro-)N-homo(phyto)ceramides

  [结构：见正文]从D-异抗坏血酸（一种常见的食品防腐剂）开始合成了一种多用途的（S）-3-（羟甲基）丁烷-1,2,4-三醇结构单元。这种方法的关键转变是通过高收率和完全区域选择性的环氧开放来引入支链。这种灵活的合成子已被精细化为一类新型的（二氢-）N-高（植物）神经酰胺。
• An Enantioselective Synthesis of (2<i>S</i>,3<i>R</i>)-3-(<i>N</i>-Benzyloxycarbonyl)amino-1-chloro-4-phenylthiobutan-2-ol, a Central Intermediate of Nelfinavir¹
  作者：Masaya Ikunaka、Jun Matsumoto、Yoshito Fujima、Yoshihiko Hirayama

  DOI：10.1021/op010073i

  日期：2002.1.1

  (2S,3R)-3-(N-Benzyloxycarbonyl)amino-1-chloro-4-phenylthiobutan-2-ol 1 is a central intermediate of nelfinavir 2, which, being a potent HIV protease inhibitor, represents one of the most clinically efficacious anti AIDS drugs. Thus, a practical enantioselective synthesis of 1 has been devised which employs sodium erythorbate 9 as a chiral starting material. Consisting of the total 14-step functional

  (2S,3R)-3-(N-Benzyloxycarbonyl)amino-1-chloro-4-phenylthiobutan-2-ol 1 是奈非那韦 2 的中心中间体，它是一种有效的 HIV 蛋白酶抑制剂，是临床上最常用的一种有效的抗艾滋病药物。因此，设计了一种实用的对映选择性合成 1，它使用异抗坏血酸钠 9 作为手性起始材料。由通过甲基 (2S,3R)-4-hydroxy-2,3-epoxybutyrate 8 进行的总共 14 步官能团操作组成，合成过程可以省去色谱纯化，并以 17% 的总产率提供结构复杂的 1严格控制立体化学。
• Synthesis of alkyl (2S,3R)-4-hydroxy-2,3-epoxybutyrates from sodium erythorbate
  作者：James Dunigan、Leland O. Weigel

  DOI：10.1021/jo00021a048

  日期：1991.10
• Cyclization of Chiral Carbon-Centered Aziridinyl Radicals: A New Route to Azirino[2',3':3,4]pyrrolo[1,2-a]indoles
  作者：Frederick E. Ziegler、Makonen Belema

  DOI：10.1021/jo00105a009

  日期：1994.12

  A carbon-centered aziridinyl radical has been generated from the ester of chiral aziridine carboxylic acid 5b. The resultant radical has been cyclized directly and has been brominated with CBrCl3. The bromo aziridines have also been cyclized reductively in the presence of n-Bu(3)SnH. Dihydroindole 8b bears the same relative and absolute stereochemistry as the mitomycin C nucleus.
• Process and intermediates for chiral epoxides
  申请人：Eli Lilly and Company

  公开号：US05097049A1

  公开（公告）日：1992-03-17

  Chiral epoxybutyrates are prepared in high yield from novel dihydro-3R-substituted sulfonyloxy-4R-hydroxy-2-(3H)furanones via based catalyzed alcoholysis. The product chiral epoxy butyrates are useful intermediates for the synthesis of 1-carba-1-dethia cephem antibiotics.

  手性环氧丁酸酯是通过基于催化的醇解法，从新型的二氢-3R-取代磺酰氧基-4R-羟基-2-(3H)呋喃酮高产率制备而成。所得的手性环氧丁酸酯是合成1-羰基-1-脱硫头孢菌素类抗生素的有用中间体。