(2S,3R)-2-Allyl-3-benzyloxycarbonylamino-succinic acid 1-methyl ester 4-(2-trimethylsilanyl-ethyl) ester | 213473-84-8

• 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,3R)-2-Allyl-3-benzyloxycarbonylamino-succinic acid 1-methyl ester 4-(2-trimethylsilanyl-ethyl) ester
• 英文别名: 1-O-methyl 4-O-(2-trimethylsilylethyl) (2R,3S)-3-(phenylmethoxycarbonylamino)-2-prop-2-enylbutanedioate
• CAS: 213473-84-8
• 化学式: C₂₁H₃₁NO₆Si
• 分子量: 421.566
• InChiKey: SSKLQFNVOOEQBL-MSOLQXFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  29
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2-Allyl-3-benzyloxycarbonylamino-succinic acid 1-methyl ester 4-(2-trimethylsilanyl-ethyl) ester 在 sodium periodate 、 四氧化锇 作用下， 生成 (2S,3R)-5-Hydroxy-pyrrolidine-1,2,3-tricarboxylic acid 1-benzyl ester 3-methyl ester 2-(2-trimethylsilanyl-ethyl) ester
  参考文献：
  名称：

  1,2-Asymmetric induction in dianionic allylation reactions of amino acid derivatives-synthesis of functionally useful, enantiopure aspartates and constrained scaffolds

  摘要：

  Dianions derived from N-Cbz aspartic acid esters undergo highly stereoselective anti allylation reactions at the unsubstituted carbon. The roles of additives, of the cation and of the electrophile were studied; Synthetic applications and potential utility in peptidomimetic design are also described. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00899-5
• 作为产物：
  描述：

  丙烯酰碘 、 (S)-2-Benzyloxycarbonylamino-succinic acid 4-methyl ester 1-(2-trimethylsilanyl-ethyl) ester 在 六甲基磷酰三胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到(2S,3R)-2-Allyl-3-benzyloxycarbonylamino-succinic acid 1-methyl ester 4-(2-trimethylsilanyl-ethyl) ester
  参考文献：
  名称：

  1,2-Asymmetric induction in dianionic allylation reactions of amino acid derivatives-synthesis of functionally useful, enantiopure aspartates and constrained scaffolds

  摘要：

  Dianions derived from N-Cbz aspartic acid esters undergo highly stereoselective anti allylation reactions at the unsubstituted carbon. The roles of additives, of the cation and of the electrophile were studied; Synthetic applications and potential utility in peptidomimetic design are also described. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00899-5

文献信息

• 1,2-Asymmetric induction in dianionic allylation reactions of amino acid derivatives-synthesis of functionally useful, enantiopure aspartates and constrained scaffolds
  作者：Stephen Hanessian、Roberto Margarita、Adrian Hall、Xuehong Luo

  DOI：10.1016/s0040-4039(98)00899-5

  日期：1998.8

  Dianions derived from N-Cbz aspartic acid esters undergo highly stereoselective anti allylation reactions at the unsubstituted carbon. The roles of additives, of the cation and of the electrophile were studied; Synthetic applications and potential utility in peptidomimetic design are also described. (C) 1998 Elsevier Science Ltd. All rights reserved.