(2S,3R)-N-Boc-N-methyl-O-benzyl-L-threonine trimethylsilyl ester | 223923-54-4

• 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-Boc-N-methyl-O-benzyl-L-threonine trimethylsilyl ester
• 英文别名: Boc-N(Me)Thr(Bn)-OEtTMS；2-trimethylsilylethyl (2S,3R)-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]-3-phenylmethoxybutanoate
• CAS: 223923-54-4
• 化学式: C₂₂H₃₇NO₅Si
• 分子量: 423.625
• InChiKey: BAEIXFGLVHQNNP-MJGOQNOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.71
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3R)-N-Boc-N-methyl-O-benzyl-L-threonine trimethylsilyl ester 在 palladium on activated charcoal N-甲基吗啉 、 2,3,5-三甲基吡啶 、 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 四丁基氟化铵 、 氢气 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 5,5-二甲基-1,3-环己二酮 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 166.0h， 生成 dimethyl (2S,5R,6S,9S,12S,13S,16R)-2-[(1R)-1-hydroxyethyl]-12-[(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dienyl]-1,6,13-trimethyl-3,7,10,14,19-pentaoxo-9-propan-2-yl-1,4,8,11,15-pentazacyclononadecane-5,16-dicarboxylate
  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：

  N-Boc-O-苄基-L-苏氨酸 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydride 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (2S,3R)-N-Boc-N-methyl-O-benzyl-L-threonine trimethylsilyl ester
  参考文献：
  名称：

  Synthesis towards microcystins and related toxins

  摘要：

  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。

  DOI：

  10.1039/cc9960001683

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.