ethyl (2S,3S)-3-benzyloxirane-2-carboxylate

• 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,3S)-3-benzyloxirane-2-carboxylate
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: VBLCHSPDSRPGCQ-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (2S,3S)-3-benzyloxirane-2-carboxylate 在 盐酸 、 三氟化硼乙醚 作用下， 以 乙醇 、 水 为溶剂， 反应 8.0h， 生成 (2S,3R)-3-氨基-2-羟基-4-苯丁酸
  参考文献：
  名称：

  Chemoenzymatic formal total synthesis of (−)-bestatin

  摘要：

  A highly stereoselective, enzymatic reduction of an alpha-chloro-beta-keto ester provided the key intermediate for a total synthesis of the alpha-hydroxy-beta-amino acid moiety of (-)-bestatin. The reduction product was cyclized to a glycidic ester that was opened in a Ritter reaction with benzonitrile, affording a trans-oxazoline, which was hydrolyzed under acidic conditions to the target molecule. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.08.022
• 作为产物：
  描述：

  ethyl 3-[(p-nitrobenzenesulfonyl)oxy]-2-oxo-4-phenylbutanoate 在 sodium tetrahydroborate 、 sodium azide 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 为溶剂， 反应 23.0h， 生成 ethyl (2S,3S)-3-benzyloxirane-2-carboxylate
  参考文献：
  名称：

  Synthesis and Reactions of 3-(Nosyloxy)-2-keto Esters

  摘要：

  A series of 3-(nosyloxy)-2-keto esters 7a-j were prepared from the corresponding cr-keto esters by conversion to the trimethylsilyl enol ether and reaction with p-nitrobenzenesulfonyl peroxide. Conversion of these materials to 1,2,3-trifunctionalized compounds is described, and comparison of their properties with isomeric 2-(nosyloxy)-3-keto esters is discussed.

  DOI：

  10.1021/jo962206h

文献信息

• An Asymmetric Catalytic Darzens Reaction between Diazoacetamides and Aldehydes Generates<i>cis</i>-Glycidic Amides with High Enantiomeric Purity
  作者：Wei-Jun Liu、Bing-Da Lv、Liu-Zhu Gong

  DOI：10.1002/anie.200903061

  日期：2009.8.17

  strength: The title reaction was catalyzed by a chiral titanium complex formed in situ from commercially available Ti(OiPr)4 and (R)‐binol, and gave cis‐glycidic amides with excellent enantiomeric purity (see scheme). This new method has been applied to the preparation of chiral building blocks used for the synthesis of the side chain of taxol and (−)‐bestatin.

  钛强度：标题反应是由由市售Ti（O i Pr）4和（R）-比诺醇原位形成的手性钛络合物催化的，得到具有出色对映体纯度的顺式-缩水甘油酰胺（参见方案）。此新方法已应用于制备用于合成紫杉醇和（-）-bestatin侧链的手性结构单元。
• Synthesis and Reactions of 3-(Nosyloxy)-2-keto Esters
  作者：Robert V. Hoffman、M. Catherine Johnson、John F. Okonya

  DOI：10.1021/jo962206h

  日期：1997.4.1

  A series of 3-(nosyloxy)-2-keto esters 7a-j were prepared from the corresponding cr-keto esters by conversion to the trimethylsilyl enol ether and reaction with p-nitrobenzenesulfonyl peroxide. Conversion of these materials to 1,2,3-trifunctionalized compounds is described, and comparison of their properties with isomeric 2-(nosyloxy)-3-keto esters is discussed.
• Chemoenzymatic formal total synthesis of (−)-bestatin
  作者：Brent D. Feske、Jon D. Stewart

  DOI：10.1016/j.tetasy.2005.08.022

  日期：2005.9

  A highly stereoselective, enzymatic reduction of an alpha-chloro-beta-keto ester provided the key intermediate for a total synthesis of the alpha-hydroxy-beta-amino acid moiety of (-)-bestatin. The reduction product was cyclized to a glycidic ester that was opened in a Ritter reaction with benzonitrile, affording a trans-oxazoline, which was hydrolyzed under acidic conditions to the target molecule. (C) 2005 Elsevier Ltd. All rights reserved.