methyl (2R,3S,4R)-4-{(Z)-1-methoxy-1-oxo-3-[(S)-1-phenylethylamino]but-2-en-2-yl}-2-methyl-5-oxo-tetrahydrofuran-3-carboxylate | 1108730-32-0

• 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: methyl (2R,3S,4R)-4-{(Z)-1-methoxy-1-oxo-3-[(S)-1-phenylethylamino]but-2-en-2-yl}-2-methyl-5-oxo-tetrahydrofuran-3-carboxylate
• 英文别名: methyl (2R,3S,4R)-4-[(Z)-1-methoxy-1-oxo-3-[[(1S)-1-phenylethyl]amino]but-2-en-2-yl]-2-methyl-5-oxooxolane-3-carboxylate
• CAS: 1108730-32-0
• 化学式: C₂₀H₂₅NO₆
• 分子量: 375.422
• InChiKey: MKNGDKYOVQZSTO-UWRWJOEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (4R,5S,Z)-4-ethyl 3,5-dimethyl 6-oxo-2-((S)-1-phenylethylamino)hept-2-ene-3,4,5-tricarboxylate 在 sodium tetrahydroborate 、 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以95%的产率得到methyl (2R,3S,4R)-4-{(Z)-1-methoxy-1-oxo-3-[(S)-1-phenylethylamino]but-2-en-2-yl}-2-methyl-5-oxo-tetrahydrofuran-3-carboxylate
  参考文献：
  名称：

  A domino reaction of a β-ketoester, phenylethylamine and ethyl glyoxylate: leading to chiral tricarboxylate containing multiple stereocenters

  摘要：

  A new type of chiral tricarboxylate containing multiple stereocenters was synthesized via the one-pot reaction of a beta-ketoester. (S)-phenylethylamine, and ethyl glyoxylate. High yields and diastereoselectivities (up to 96:4 dr) were obtained under optimal conditions. The reaction of the chiral tricarboxylate with Zn(BH4)(2) gave chiral gamma-lactones in good yields With Lip to 92:8 dr. The structures and configurations of the new chiral tricarboxylates were characterized by X-ray diffraction analysis. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.10.028