(2S,4S)-2-(di(tert-butoxycarbonyl)amino)-5-hydroxy-4-methylpentanoic acid tert-butyl ester | 159415-79-9

• 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,4S)-2-(di(tert-butoxycarbonyl)amino)-5-hydroxy-4-methylpentanoic acid tert-butyl ester
• 英文别名: tert-butyl (2S,4S)-2-[bis[(2-methylpropan-2-yl)oxycarbonyl]amino]-5-hydroxy-4-methylpentanoate
• CAS: 159415-79-9
• 化学式: C₂₀H₃₇NO₇
• 分子量: 403.516
• InChiKey: SEGLXPRFMGSJTN-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,4S)-2-(di(tert-butoxycarbonyl)amino)-5-hydroxy-4-methylpentanoic acid tert-butyl ester 在 molecular sieve 、 戴斯-马丁氧化剂 、 一水合肼 作用下， 以 盐酸 、 二氯甲烷 为溶剂， 生成 (2S,4S)-5,5-dichloroleucine
  参考文献：
  名称：

  A study of polychlorinated leucine derivatives: synthesis of (2S,4S)-5,5-dichloroleucine

  摘要：

  The first total synthesis of (2S,4S)-5,5-dichloroleucine has been achieved in 11 steps from L-pyroglutamic acid. A key step is the dichlorination process on the hydrazone of aldehyde 13 with CuCl2 in triethylamine. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.02.118
• 作为产物：
  描述：

  Boc-L-谷氨酸-1-叔丁酯 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 四(三苯基膦)钯 、 正丁基锂 、 dimethyl sulfide borane 、 caesium carbonate 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 乙醚 、 乙腈 为溶剂， 反应 79.0h， 生成 (2S,4S)-2-(di(tert-butoxycarbonyl)amino)-5-hydroxy-4-methylpentanoic acid tert-butyl ester
  参考文献：
  名称：

  Total Synthesis of the Chlorinated Marine Natural Product Dysamide B

  摘要：

  [GRAPHICS]Two approaches to the synthesis of (2S,4S)-5,5-dichloroleucine are compared, and the parent amino acid was used in the first total synthesis of the polychlorinated marine natural product, dysamide B. A key step was the lead tetraacetate-mediated decarboxylation of an alpha, alpha-dichloro acid in the presence of 1,4-cyclohexadiene to generate the dichloromethyl group.

  DOI：

  10.1021/ol062279f

文献信息

• Synthesis of (2S,4S)-5-Fluoroleucine
  作者：Claire M. Moody、Bernard A. Starkmann、Douglas W. Young

  DOI：10.1016/s0040-4039(00)73531-3

  日期：1994.7

  (2S,4S)-5-Fluoroleucine, has been prepared by stereospecific synthesis using (2S)pyroglutamic acid as a chiral template. Protection was required in the synthesis to prevent cyclisation to a proline derivative during the fluorination step.

  (2S,4S)-5-氟亮氨酸已通过立体选择性合成制备，其中采用了(2S)吡咯 glutamic acid 作为手性模板。在合成过程中需要进行保护，以防止在氟化步骤中形成脯氨酸衍生物。
• ¹⁹F Nuclear Magnetic Resonance Chemical Shifts of Fluorine Containing Aliphatic Amino Acids in Proteins:  Studies on <i>Lactobacillus casei</i> Dihydrofolate Reductase Containing (2<i>S</i>,4<i>S</i>)-5-Fluoroleucine
  作者：James Feeney、John E. McCormick、Christopher J. Bauer、Berry Birdsall、Claire M. Moody、Bernard A. Starkmann、Douglas W. Young、Peter Francis、Robert H. Havlin、William D. Arnold、Eric Oldfield

  DOI：10.1021/ja960465i

  日期：1996.1.1

  DHFR, covering a chemical shift range of 15 ppm. The large range of chemical shifts observed could not be explained solely in terms of the electrostatic field effects due to local charge fields and is thought to have a second contribution from side-chain conformational differences (γ-gauche effects) between different leucine residues, making 19F NMR of aliphatic amino acids in proteins a potentially

  我们制备了含有生物合成结合的 (2S,4S)-5-氟亮氨酸 ([5-F]-Leu DHFR) 的干酪乳杆菌二氢叶酸还原酶，并在 9.4 特斯拉获得了其 1H 和 19F NMR 光谱。[5-F]-Leu DHFR 的 19F 光谱显示 DHFR 中 13 个亮氨酸残基的 12 个相当尖锐的峰（一个包含两个重叠信号），覆盖了 15 ppm 的化学位移范围。观察到的大范围化学位移不能仅用由于局部电荷场引起的静电场效应来解释，并且被认为具有来自不同亮氨酸残基之间的侧链构象差异（γ-gauche 效应）的第二个贡献，使得蛋白质中脂肪族氨基酸的 19F NMR 是一种潜在有用的蛋白质结构新探针。
• A study of polychlorinated leucine derivatives: synthesis of (2S,4S)-5,5-dichloroleucine
  作者：Ana Ardá、Carlos Jiménez、Jaime Rodrı́guez

  DOI：10.1016/j.tetlet.2004.02.118

  日期：2004.4

  The first total synthesis of (2S,4S)-5,5-dichloroleucine has been achieved in 11 steps from L-pyroglutamic acid. A key step is the dichlorination process on the hydrazone of aldehyde 13 with CuCl2 in triethylamine. (C) 2004 Elsevier Ltd. All rights reserved.
• Total Synthesis of the Chlorinated Marine Natural Product Dysamide B
  作者：Amanda C. Durow、G. Cliona Long、Susan J. O'Connel、Christine L. Willis

  DOI：10.1021/ol062279f

  日期：2006.11.9

  [GRAPHICS]Two approaches to the synthesis of (2S,4S)-5,5-dichloroleucine are compared, and the parent amino acid was used in the first total synthesis of the polychlorinated marine natural product, dysamide B. A key step was the lead tetraacetate-mediated decarboxylation of an alpha, alpha-dichloro acid in the presence of 1,4-cyclohexadiene to generate the dichloromethyl group.