(2S,3R)-N-tert-butoxycarbonyl-2-methyl-3-amino-4-hydroxy methyl butanoate | 134440-96-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3R)-N-tert-butoxycarbonyl-2-methyl-3-amino-4-hydroxy methyl butanoate
• 英文别名: (2S,3R)-methyl 3-(tert-butoxycarbonyl)amino-4-hydroxy-2-methylbutyrate；methyl (2S,3R)-4-hydroxy-2-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate
• CAS: 134440-96-3
• 化学式: C₁₁H₂₁NO₅
• 分子量: 247.291
• InChiKey: HDZXPRVVYKAUMX-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3R)-N-tert-butoxycarbonyl-2-methyl-3-amino-4-hydroxy methyl butanoate 在 chromium dichloride 、 2,3,5-三甲基吡啶 、 lithium hydroxide 、 四(三苯基膦)钯 、 草酰氯 、 thallium (I) ethoxide 、 溶剂黄146 、 二甲基亚砜 、 N,N'-二环己基碳二亚胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 锌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 115.0h， 生成 methyl (2R,3S)-2-[[(2S)-2-[[(2R)-2-[2-[[(4R)-5-methoxy-4-[[(2S,3S,4E,6E,8S,9S)-9-methoxy-2,6,8-trimethyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]-10-phenyldeca-4,6-dienoyl]amino]-5-oxopentanoyl]-methylamino]prop-2-enoylamino]propanoyl]amino]-4-methylpentanoyl]amino]-3-methyl-4-oxo-4-[[(2S)-1-oxo-1-(2,3,4,5,6-pentafluorophenoxy)propan-2-yl]amino]butanoate
  参考文献：
  名称：

  丝氨酸-苏氨酸磷酸酶抑制剂微囊藻毒素-LA的全合成

  摘要：

  由激酶和磷酸酶介导的可逆蛋白磷酸化是细胞的主要控制元件。有多种有毒的天然产物会抑制某些磷酸酶，从而破坏正常的生化途径。这些毒素可用于剖析与这些酶中的每一种相关的个体生化途径。本文描述了一种此类毒素的首次全合成，即环状七肽微囊藻毒素-LA。该合成具有收敛路线，可用于寻找选择性磷酸酶抑制剂的类似物制备。描述了一种不寻常的氨基酸 Adda 的新途径，它通过 Suzuki 偶联反应结合了有效的非对映选择性天冬氨酸烷基化和二烯合成。

  DOI：

  10.1021/ja961683e
• 作为产物：
  描述：

  methyl (2S,3R)-3-(N-Boc-amino)-4-(tert-butyldimethylsilyloxy)-2-methyl-butanoate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以84%的产率得到(2S,3R)-N-tert-butoxycarbonyl-2-methyl-3-amino-4-hydroxy methyl butanoate
  参考文献：
  名称：

  Total Synthesis of Motuporin and 5-[l-Ala]-Motuporin

  摘要：

  Total synthesis of the cyclic peptide hepatotoxin motuporin is described, including an efficient synthesis of the constituent amino acid Adda. Three strategies to motuporin are outlined with their relative strengths and weaknesses. Cyclization of the linear peptide precursor was found to proceed moderately well for peptides containing the N-methyldehydrobutyrine residue masked as a threonine, but significant C-terminal epimerization occurred in the presence of the dehydroamino acid. Replacement of the N-methyldehydrobutyrine residue by L-alanine was explored to assess the contribution of this dehydroamino acid to the biochemical activity of motuporin. Some epimerization also was observed during cyclization of the alanine-containing peptide. Synthetic motuporin and both isomers of 5-[L-Ala]-motuporin inhibit the activity of protein phosphatase-l (PP1) in rat adipocyte lysates with comparable IC50 values. These results indicate that the N-methyldehydrobutyrine residue is not essential for PP1 inhibition.

  DOI：

  10.1021/jo982145i

文献信息

• Stereocontrolled synthesis of (2S, 3S, 8S, 9S)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyldeca-4E,6E-dienoic acid (ADDA), the characteristic amino acid of microcystins and nodularin
  作者：Mark F. Beatty、Clive Jennings-White、Mitchell A. Avery

  DOI：10.1039/c39910000351

  日期：——

  (4R,5S)-4-Methyl-5-phenyloxazolidin-2-one was used as a chiral template to construct the 8S and 9S chiral centres of (2S,3S,8S,9S)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyldeca-4,6-dienoic acid (ADDA), the 2S and 3S centres were derived from D-aspartic acid.

  以（4 R，5 S）-4-甲基-5-苯基恶唑烷丁-2-酮为手性模板，构建（2 S，3 S，8 S，9 S）-的8 S和9 S手性中心。3-氨基-9-甲氧基-2,6,8-三甲基-10-苯基癸-4,6-二烯酸（ADDA）的2 S和3 S中心衍生自D-天门冬氨酸。
• Stereocontrolled synthesis of (2S,3S,8S,9S,4E,6E)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyldeca-4,6-dienoic acid (Adda), the amino acid characteristic of microcystins and nodularin
  作者：Vlark F. Beatty、Clive Jennings-White、Mitchell A. Avery

  DOI：10.1039/p19920001637

  日期：——

  (4R,5S)-4-Methyl-5-phenyloxazolindin-2-one has been used as a chiral template to construct the 8S and 9S chiral centres of (2S,3S,8S,9S)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyldeca-4,6-dienoic acid (Adda), the 2S and 3S centres being derived from D-aspartic acid.

  （4 R，5 S）-4-甲基-5-苯基恶唑啉丁-2-一已被用作手性模板来构建（2 S，3 S，8 S，9 S）的8 S和9 S手性中心-3-氨基-9-甲氧基-2,6,8-三甲基-10-苯基癸基-4,6-二烯酸（Adda），其2 S和3 S中心衍生自D-天门冬氨酸。
• A novel stereoselective route to some uncommon amino acids
  作者：Clay Pearson、Kenneth L Rinehart、Michihiro Sugano

  DOI：10.1016/s0040-4039(98)02383-1

  日期：1999.1

  of ad-erythro-β-methylaspartic acid analog was achieved in six steps from commercially available material. Evans' aldol reactions were utilized followed by Weinreb amide formation and Mitsunobu inversion to achieve the necessary stereochemistry of the amino acid target. The technique was applied to the synthesis of an aspartic acid analog as well as a diaminobutyric acid analog.

  用市售材料通过六个步骤即可高效合成赤型-β-甲基天冬氨酸类似物。利用埃文斯的醛醇缩合反应，随后形成韦氏脲酰胺和光延反转，以实现氨基酸靶标的必要立体化学。该技术被应用于天冬氨酸类似物以及二氨基丁酸类似物的合成。
• A new stereoselective route to (2S, 3S, 8S, 9S, 4E, 6E)-3-amino-9-methoxy-2, 6, 8-trimethyl-10-phenyldeca-4, 6-dienoic acid (Adda)
  作者：Hong Yong Kim、Peter L. Toogood

  DOI：10.1016/0040-4039(96)00282-1

  日期：1996.4

  N-Boc-Adda has been prepared in 15 steps and 9% overall yield from the readily available alcohol, 3-pentyne-2-ol, employing a route that includes two Claisen rearrangements.

  使用包括两个克莱森重排的途径，由15种步骤制备N -Boc-Adda，总产率为9％，由现成的醇3-pentyne-2-ol制备。
• Total Synthesis of the Serine-Threonine Phosphatase Inhibitor Microcystin-LA
  作者：John M. Humphrey、James B. Aggen、A. Richard Chamberlin

  DOI：10.1021/ja961683e

  日期：1996.1.1

  element of the cell. There is a diverse group of toxic natural products that inhibit certain phosphatases, thereby disrupting normal biochemical pathways. These toxins can be useful for dissecting the individual biochemical pathways associated with each of these enzymes. This Article describes the first total synthesis of one such toxin, the cyclic heptapeptide microcystin-LA. The synthesis features a convergent

  由激酶和磷酸酶介导的可逆蛋白磷酸化是细胞的主要控制元件。有多种有毒的天然产物会抑制某些磷酸酶，从而破坏正常的生化途径。这些毒素可用于剖析与这些酶中的每一种相关的个体生化途径。本文描述了一种此类毒素的首次全合成，即环状七肽微囊藻毒素-LA。该合成具有收敛路线，可用于寻找选择性磷酸酶抑制剂的类似物制备。描述了一种不寻常的氨基酸 Adda 的新途径，它通过 Suzuki 偶联反应结合了有效的非对映选择性天冬氨酸烷基化和二烯合成。