methyl E-(2S,3R)-(N-Boc-amino)-3-methyl-4-hexenoate | 176908-07-9

• 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: methyl E-(2S,3R)-(N-Boc-amino)-3-methyl-4-hexenoate
• 英文别名: methyl (E,2R,3R)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]hex-4-enoate
• CAS: 176908-07-9
• 化学式: C₁₃H₂₃NO₄
• 分子量: 257.33
• InChiKey: ORRUSLRUWVAHDD-WENXHQBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl E-(2S,3R)-(N-Boc-amino)-3-methyl-4-hexenoate 在 咪唑 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 臭氧 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.75h， 生成 methyl (2S,3R)-3-(N-Boc-amino)-4-(tert-butyldimethylsilyloxy)-2-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
• 作为产物：
  描述：

  methyl (2R*,3R*)-2-methoxy-3-methylhex-4-enoate 在 二苯基磷酸 、 三溴化硼 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 methyl E-(2S,3R)-(N-Boc-amino)-3-methyl-4-hexenoate
  参考文献：
  名称：

  （2 S，3 S，8 S，9 S，4 E，6 E）-3-氨基-9-甲氧基-2、6、8-三甲基-10-苯基癸4、6-二烯酸的新的立体选择性途径酸（阿达）

  摘要：

  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。

  DOI：

  10.1016/0040-4039(96)00282-1

文献信息

• Synthesis towards microcystins and related toxins
  作者：Hong Yong Kim、Karin Stein、Peter L. Toogood

  DOI：10.1039/cc9960001683

  日期：——

  A general route is described for the preparation of microcystins and nodularins, including new chemistry for the preparation of β-methyl-D-aspartic acid.

  文中描述了一般制备微囊藻毒素和节球藻毒素的路线，包括制备β-甲基-D-天冬氨酸的新化学方法。
• Total Synthesis of Motuporin and 5-[<scp>l</scp>-Ala]-Motuporin
  作者：Raghu Samy、Hong Yong Kim、Matthew Brady、Peter L. Toogood

  DOI：10.1021/jo982145i

  日期：1999.4.1

  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.
• 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。