1-O-tert-butyl 2-O-methyl (2R,4S)-4-[tert-butyl(dimethyl)silyl]oxy-5-hydroxypyrrolidine-1,2-dicarboxylate | 1138344-12-3

• 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: 1-O-tert-butyl 2-O-methyl (2R,4S)-4-[tert-butyl(dimethyl)silyl]oxy-5-hydroxypyrrolidine-1,2-dicarboxylate
• CAS: 1138344-12-3
• 化学式: C₁₇H₃₃NO₆Si
• 分子量: 375.538
• InChiKey: XLZKADXQFSDGBF-OJRHAOMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-O-tert-butyl 2-O-methyl (2R,4S)-4-[tert-butyl(dimethyl)silyl]oxy-5-hydroxypyrrolidine-1,2-dicarboxylate 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以63%的产率得到1-(tert-butyl) 2-methyl (2R,4S)-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-1,2-dicarboxylate
  参考文献：
  名称：

  Concise syntheses of enantiomerically pure protected 4-hydroxypyroglutamic acid and 4-hydroxyproline from a nitroso-cyclopentadiene cycloadduct

  摘要：

  O-TBS-protected methyl trans-4-hydroxypyroglutamate and methyl trans-4-hydroxyproline ester were synthesized from nitroso-cyclopentadiene Diels-Alder cycloadducts. Enzymatic resolution of the key intermediate, 4-amino-cyclopent-2-enol, provides access to both L- and D-amino acids. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.12.013
• 作为产物：
  描述：

  4-(tert-butyldimethylsilanyloxy)-5-oxopyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 在 lithium triethoxyborohydride 、 双氧水 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 生成 1-O-tert-butyl 2-O-methyl (2R,4S)-4-[tert-butyl(dimethyl)silyl]oxy-5-hydroxypyrrolidine-1,2-dicarboxylate
  参考文献：
  名称：

  Concise syntheses of enantiomerically pure protected 4-hydroxypyroglutamic acid and 4-hydroxyproline from a nitroso-cyclopentadiene cycloadduct

  摘要：

  O-TBS-protected methyl trans-4-hydroxypyroglutamate and methyl trans-4-hydroxyproline ester were synthesized from nitroso-cyclopentadiene Diels-Alder cycloadducts. Enzymatic resolution of the key intermediate, 4-amino-cyclopent-2-enol, provides access to both L- and D-amino acids. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.12.013

文献信息

• Concise syntheses of enantiomerically pure protected 4-hydroxypyroglutamic acid and 4-hydroxyproline from a nitroso-cyclopentadiene cycloadduct
  作者：Weiqiang Huang、Marvin J. Miller

  DOI：10.1016/j.tetasy.2008.12.013

  日期：2008.12

  O-TBS-protected methyl trans-4-hydroxypyroglutamate and methyl trans-4-hydroxyproline ester were synthesized from nitroso-cyclopentadiene Diels-Alder cycloadducts. Enzymatic resolution of the key intermediate, 4-amino-cyclopent-2-enol, provides access to both L- and D-amino acids. (C) 2008 Elsevier Ltd. All rights reserved.