(R,E)-tert-butyl 4-(4-ethoxy-4-oxobut-2-en-2-yl)-2,2-dimethyloxazolidine-3-carboxylate | 1168208-13-6

• 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: (R,E)-tert-butyl 4-(4-ethoxy-4-oxobut-2-en-2-yl)-2,2-dimethyloxazolidine-3-carboxylate
• 英文别名: (R)-4-((E)-2-ethoxycarbonyl-1-methyl-vinyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester；tert-butyl (4R)-4-[(E)-4-ethoxy-4-oxobut-2-en-2-yl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 1168208-13-6
• 化学式: C₁₆H₂₇NO₅
• 分子量: 313.394
• InChiKey: VOAXVVNERNLFSN-ZKQHCESOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-甲氧基-N-甲基-N2-{[(2-甲基-2-丙基)氧基]羰基}-L-丝氨酰胺 在 三氟化硼乙醚 、 sodium hydride 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 7.0h， 生成 (R,Z)-tert-butyl 4-(4-ethoxy-4-oxobut-2-en-2-yl)-2,2-dimethyloxazolidine-3-carboxylate 、 (R,E)-tert-butyl 4-(4-ethoxy-4-oxobut-2-en-2-yl)-2,2-dimethyloxazolidine-3-carboxylate
  参考文献：
  名称：

  Studies toward asymmetric synthesis of leiodelide A

  摘要：

  An enantioselective route for oxazoline 4, a key fragment toward the asymmetric synthesis of leiodelide A, is described. We synthesized northern subunit 6 through a Julia-Lythgoe olefination and subsequent Sharpless asymmetric dihydroxylation. Moreover, a highly diastereoselective method using well-established Evans' asymmetric aldol condensation was developed for preparation of southern fragment 5. The additional feature of this synthetic route is the formation of oxazoline 4 through DAST-promoted cyclization of the amidation product from subunits 5 and 6. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.10.102

文献信息

• Enantioselective Organocatalytic Conjugate Reduction of β-Azole-Containing α,β-Unsaturated Aldehydes
  作者：Thomas J. Hoffman、Jyotirmayee Dash、James H. Rigby、Stellios Arseniyadis、Janine Cossy

  DOI：10.1021/ol900893e

  日期：2009.7.2

  β-Azole-containing α,β-unsaturated aldehydes were successfully reduced under highly enantioselective organocatalytic transfer hydrogenation conditions. The products were obtained in good yields and up to 94% optical purity. This simple process was successfully applied to the synthesis of the C7−C14 fragment of ulapualide A, a natural product which exhibits promising antitumor activity.

  在高度对映选择性的有机催化转移氢化条件下，成功还原了含β-Azole的α，β-不饱和醛。以高产率和高达94％的光学纯度获得产物。这个简单的过程已成功地应用于乌拉泊利德A的C7-C14片段的合成，该产品是天然的，具有良好的抗肿瘤活性。
• Studies toward asymmetric synthesis of leiodelide A
  作者：Rong-Guo Ren、Ming Li、Chang-Mei Si、Zhuo-Ya Mao、Bang-Guo Wei

  DOI：10.1016/j.tetlet.2014.10.102

  日期：2014.12

  An enantioselective route for oxazoline 4, a key fragment toward the asymmetric synthesis of leiodelide A, is described. We synthesized northern subunit 6 through a Julia-Lythgoe olefination and subsequent Sharpless asymmetric dihydroxylation. Moreover, a highly diastereoselective method using well-established Evans' asymmetric aldol condensation was developed for preparation of southern fragment 5. The additional feature of this synthetic route is the formation of oxazoline 4 through DAST-promoted cyclization of the amidation product from subunits 5 and 6. (C) 2014 Elsevier Ltd. All rights reserved.