(2S,4S)-4-tert-butoxycarbonylamino-2-methyl-2-pentanoic acid | 198976-13-5

• 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,4S)-4-tert-butoxycarbonylamino-2-methyl-2-pentanoic acid
• 英文别名: (2S,4S)-2-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid
• CAS: 198976-13-5
• 化学式: C₁₁H₂₁NO₄
• 分子量: 231.292
• InChiKey: KYUSXVZOJPHPBF-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,4S)-4-tert-butoxycarbonylamino-2-methyl-2-pentanoic acid 在 N-甲基吗啉 、 伯吉斯试剂 、 乌洛托品 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 copper(ll) bromide 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 13.92h， 生成 2-((1S,3S)-3-tert-Butoxycarbonylamino-1-methyl-butyl)-oxazole-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of the C₂₆−C₃₂ Oxazole Fragment of Calyculin C:  A Test Case for Oxazole Syntheses

  摘要：

  The synthesis of the C-26-C-32 oxazole fragment 4 and its C-32 epimer 20 of serine/threonine protein phosphatase PP1 and PP2A inhibitor calyculin C is presented. The syn methyl arrangement in 4 was established through cyclic stereocontrol. Several methods for oxidizing the intermediate oxazolines 18 and 19 to the finished oxazole fragments were explored. The best results were obtained with oxidations proceeding through the corresponding ester enolate when the carbamate NH side chain was temporarily protected with a TMS group, or with CuBr2/DBU/HMTA-based oxidations. The finished oxazole fragment 4 was obtained in 21% overall yield, starting from Boc-D-alaninal.

  DOI：

  10.1021/jo971167m
• 作为产物：
  描述：

  (S)-4-tert-Butoxycarbonylamino-2-methyl-pentanoic acid methyl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 16.0h， 以61%的产率得到(2S,4S)-4-tert-butoxycarbonylamino-2-methyl-2-pentanoic acid
  参考文献：
  名称：

  Synthesis of the C₂₆−C₃₂ Oxazole Fragment of Calyculin C:  A Test Case for Oxazole Syntheses

  摘要：

  The synthesis of the C-26-C-32 oxazole fragment 4 and its C-32 epimer 20 of serine/threonine protein phosphatase PP1 and PP2A inhibitor calyculin C is presented. The syn methyl arrangement in 4 was established through cyclic stereocontrol. Several methods for oxidizing the intermediate oxazolines 18 and 19 to the finished oxazole fragments were explored. The best results were obtained with oxidations proceeding through the corresponding ester enolate when the carbamate NH side chain was temporarily protected with a TMS group, or with CuBr2/DBU/HMTA-based oxidations. The finished oxazole fragment 4 was obtained in 21% overall yield, starting from Boc-D-alaninal.

  DOI：

  10.1021/jo971167m

文献信息

• Conformational analysis of 4-amido-2,4-dimethylbutyric acid derivatives
  作者：Reinhard W. Hoffmann、Francisco Caturla、Miguel A. Lazaro、Eric Framery、M. Carmen Bernabeu、Ingrid Valancogne、Christian A. G. N. Montalbetti

  DOI：10.1039/a910179i

  日期：——

  Both syn- and anti-4-amido-2,4-dimethylbutyric acid derivatives 5 and 6 were found to populate a conformation in which the amido group is gauche to the main chain of the molecule. In the anti series (6) a single conformation predominates, in which the acid carbonyl group is also gauche to the main chain. In the syn series (5) two local conformers prevail about the C-2–C-3 bond.

  研究发现，同系和反系 4-氨基-2,4-二甲基丁酸衍生物 5 和 6 都有一个氨基与分子主链同向的构象。在反系列（6）中，一种单一的构象占主导地位，其中的酸羰基也与主链呈高位。在同系列（5）中，C-2-C-3 键的两个局部构象占主导地位。
• Schuemacher; Hoffmann, Synthesis, 2001, # 2, p. 243 - 246
  作者：Schuemacher、Hoffmann

  DOI：——

  日期：——
• Synthesis of the C₂₆−C₃₂ Oxazole Fragment of Calyculin C:  A Test Case for Oxazole Syntheses
  作者：Petri M. Pihko、Ari M. P. Koskinen

  DOI：10.1021/jo971167m

  日期：1998.1.1

  The synthesis of the C-26-C-32 oxazole fragment 4 and its C-32 epimer 20 of serine/threonine protein phosphatase PP1 and PP2A inhibitor calyculin C is presented. The syn methyl arrangement in 4 was established through cyclic stereocontrol. Several methods for oxidizing the intermediate oxazolines 18 and 19 to the finished oxazole fragments were explored. The best results were obtained with oxidations proceeding through the corresponding ester enolate when the carbamate NH side chain was temporarily protected with a TMS group, or with CuBr2/DBU/HMTA-based oxidations. The finished oxazole fragment 4 was obtained in 21% overall yield, starting from Boc-D-alaninal.