(2S,3R)-N-tert-butyloxycarbonyl-3-methylaspartic acid dimethyl ester | 149598-20-9

• 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)-N-tert-butyloxycarbonyl-3-methylaspartic acid dimethyl ester
• 英文别名: dimethyl (2R,3S)-2-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]butanedioate
• CAS: 149598-20-9
• 化学式: C₁₂H₂₁NO₆
• 分子量: 275.302
• InChiKey: UYRDCVHVAHEWBD-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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)-N-tert-butyloxycarbonyl-3-methylaspartic acid dimethyl ester 在 sodium carbonate 、 乙酰氯 作用下， 以 甲醇 、 水 为溶剂， 反应 10.0h， 生成 (2S,3R)-2-(((benzyloxy)carbonyl)amino)-4-methoxy-3-methyl-4-oxobutanoic acid
  参考文献：
  名称：

  Synthesis of Optically Active 2-Alkyl-3,4-iminobutanoic Acids. β-Amino Acids Containing an Aziridine Heterocycle

  摘要：

  All four stereoisomers of 2-alkyl-3,4-iminobutanoic acid, a novel class of beta -amino acids bearing a chemically versatile aziridine ring, were synthesized starting with aspartic acid. The synthetic strategy involves the introduction of an alkyl group at the beta -position of fully protected optically active aspartic acid followed by the construction of an aziridine ring making use of the alpha -carboxylate and alpha -amino groups. The alpha -carboxylate was reduced to the corresponding alcohol, which was then subjected to cyclization to form an aziridine ring with the N-protected amino group. Removal of the protection groups yielded the target compounds.

  DOI：

  10.1021/jo0014055
• 作为产物：
  描述：

  (E)-(2S,3S)-2-(Benzhydrylidene-amino)-3-methyl-5-phenyl-pent-4-enoic acid methyl ester 在 chromium(VI) oxide 、 盐酸 、 硫酸 、 sodium carbonate 、 臭氧 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 水 、 乙酸乙酯 、 丙酮 为溶剂， 反应 5.67h， 生成 (2S,3R)-N-tert-butyloxycarbonyl-3-methylaspartic acid dimethyl ester
  参考文献：
  名称：

  钯催化的氨基酸衍生物在α和β位置具有邻位手性季碳和叔碳中心的氨基酸衍生物的结构

  摘要：

  钯催化了（R）-2-乙酰氧基-4-芳基-3-丁烯与N-（二苯基亚甲基）甘氨酸和N-（二苯基亚甲基）丙氨酸的区域和非对映选择性烯丙基烷基化。立体化学通过使用邻-（二苯基膦基）羧酸来控制，并产生了在α和β位置具有邻位手性季碳和叔碳中心的新氨基酸衍生物。

  DOI：

  10.1016/j.tetlet.2005.07.139

文献信息

• Synthesis of optically active β-alkyl aspartate via [3,3] sigmatropic rearrangement of α-acyloxytrialkylsilane
  作者：Kazuhiko Sakaguchi、Masahiro Yamamoto、Tetsuo Kawamoto、Takeshi Yamada、Tetsuro Shinada、Keiko Shimamoto、Yasufumi Ohfune

  DOI：10.1016/j.tetlet.2004.05.157

  日期：2004.7

  The synthesis of four types of optically active beta-carbon-substituted analogs of threo-beta-hydroxy aspartate (THA) and a beta-carbon- substituted analog of threo-beta-benzyloxy aspartate (TBOA), which are potent blockers of excitatory amino acid transporters in the mammalian central nervous system, via the chirality-transferring ester-enolate Claisen rearrangement of alpha-acyloxytrialkylsilane is described. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of Optically Active 2-Alkyl-3,4-iminobutanoic Acids. β-Amino Acids Containing an Aziridine Heterocycle
  作者：Jeong-il Park、Guan Rong Tian、Dong H. Kim

  DOI：10.1021/jo0014055

  日期：2001.6.1

  All four stereoisomers of 2-alkyl-3,4-iminobutanoic acid, a novel class of beta -amino acids bearing a chemically versatile aziridine ring, were synthesized starting with aspartic acid. The synthetic strategy involves the introduction of an alkyl group at the beta -position of fully protected optically active aspartic acid followed by the construction of an aziridine ring making use of the alpha -carboxylate and alpha -amino groups. The alpha -carboxylate was reduced to the corresponding alcohol, which was then subjected to cyclization to form an aziridine ring with the N-protected amino group. Removal of the protection groups yielded the target compounds.
• Palladium-catalyzed construction of amino acid derivatives possessing vicinal chiral quaternary and tertiary carbon centers at the α and β positions
  作者：Daiji Ikeda、Motoi Kawatsura、Junichi Uenishi

  DOI：10.1016/j.tetlet.2005.07.139

  日期：2005.9

  The palladium catalyzed regio- and diastereo-selective allylic alkylation of (R)-2-acetoxy-4-aryl-3-butene with N-(diphenylmethylidene)glycinate and N-(diphenylmethylidene)alaninate occurred. The stereochemistry was controlled by the use of o-(diphenylphosphino)carboxylic acid, and produced new amino acid derivatives possessing vicinal chiral quaternary and tertiary carbon centers at the α and β positions

  钯催化了（R）-2-乙酰氧基-4-芳基-3-丁烯与N-（二苯基亚甲基）甘氨酸和N-（二苯基亚甲基）丙氨酸的区域和非对映选择性烯丙基烷基化。立体化学通过使用邻-（二苯基膦基）羧酸来控制，并产生了在α和β位置具有邻位手性季碳和叔碳中心的新氨基酸衍生物。