(2S,3S,4R)-methyl 3-((benzyloxy)methyl)-1,4-dimethyl-5-oxopyrrolidine-2-carboxylate | 1140895-26-6

• 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: (2S,3S,4R)-methyl 3-((benzyloxy)methyl)-1,4-dimethyl-5-oxopyrrolidine-2-carboxylate
• 英文别名: methyl (2S,3S,4R)-1,4-dimethyl-5-oxo-3-(phenylmethoxymethyl)pyrrolidine-2-carboxylate
• CAS: 1140895-26-6
• 化学式: C₁₆H₂₁NO₄
• 分子量: 291.347
• InChiKey: RGMRKRCMUJCXEK-XBFCOCLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl (2S,3S,4R)-3-((benzyloxy)methyl)-4-methyl-5-oxopyrrolidine-2-carboxylate 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.08h， 以47%的产率得到(2S,3S,4R)-methyl 3-((benzyloxy)methyl)-1,4-dimethyl-5-oxopyrrolidine-2-carboxylate
  参考文献：
  名称：

  Efficient asymmetric synthesis of the functionalized pyroglutamate core unit common to oxazolomycin and neooxazolomycin using Michael reaction of nucleophilic glycine Schiff base with α,β-disubstituted acrylate

  摘要：

  The functionalized pyroglutamate core unit, (2R,4R)-3, which could be converted into the beta-lactone/pyrrolidine or gamma-lactone/pyrrolidine ring system of oxazolomycin A 1 and neooxazolomycin 2, and which possesses an exomethylene group at C3 as a scaffold for the Construction of their C3 polyene segment, was synthesized by the Michael reaction of a glycine Schiff base 4 with the alpha,beta-disubstituted acrylate 8 as the key step. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.11.036

文献信息

• Efficient asymmetric synthesis of the functionalized pyroglutamate core unit common to oxazolomycin and neooxazolomycin using Michael reaction of nucleophilic glycine Schiff base with α,β-disubstituted acrylate
  作者：Takeshi Yamada、Kazuhiko Sakaguchi、Tetsuro Shinada、Yasufumi Ohfune、Vadim A. Soloshonok

  DOI：10.1016/j.tetasy.2008.11.036

  日期：2008.12

  The functionalized pyroglutamate core unit, (2R,4R)-3, which could be converted into the beta-lactone/pyrrolidine or gamma-lactone/pyrrolidine ring system of oxazolomycin A 1 and neooxazolomycin 2, and which possesses an exomethylene group at C3 as a scaffold for the Construction of their C3 polyene segment, was synthesized by the Michael reaction of a glycine Schiff base 4 with the alpha,beta-disubstituted acrylate 8 as the key step. (C) 2008 Elsevier Ltd. All rights reserved.