(2S,3S)-2-(((benzyloxy)carbonyl)amino)-3-(((3aR,4S,6R,6aR)-6-(((tert-butoxycarbonyl)amino)methyl)-2,2-diethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)-3-((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-bis((triisopropylsilyl)oxy)tetrahydrofuran-2-yl)propanoic acid | 1612257-27-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S)-2-(((benzyloxy)carbonyl)amino)-3-(((3aR,4S,6R,6aR)-6-(((tert-butoxycarbonyl)amino)methyl)-2,2-diethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)-3-((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-bis((triisopropylsilyl)oxy)tetrahydrofuran-2-yl)propanoic acid
• CAS: 1612257-27-8
• 化学式: C₅₂H₈₆N₄O₁₅Si₂
• 分子量: 1063.44
• InChiKey: XKSZEGXYDCKJIQ-JUUIELHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.87
• 重原子数：
  73.0
• 可旋转键数：
  23.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  233.43
• 氢给体数：
  4.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-(((benzyloxy)carbonyl)amino)-3-(((3aR,4S,6R,6aR)-6-(((tert-butoxycarbonyl)amino)methyl)-2,2-diethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)-3-((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-bis((triisopropylsilyl)oxy)tetrahydrofuran-2-yl)propanoic acid 、 (2R,3S,E)-1-(benzyloxy)-3-((tert-butyldimethylsilyl)oxy)-N-methyl-5-phenylpent-4-en-2-amine 在 碳酸氢钠 、 3-(二乙氧基邻酰氧基)-1,2,3-苯并三嗪-4-酮 作用下， 以 四氢呋喃 为溶剂， 反应 45.0h， 以90%的产率得到benzyl ((1S,2S)-1-(((3aR,4S,6R,6aR)-6-(tert-butoxycarbonylaminomethyl)-2,2-diethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)-3-(((2R,3S,E)-1-(benzyloxy)-3-((tert-butyldimethylsilyl)oxy)-5-phenylpent-4-en-2-yl)(methyl)amino)-1-((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-bis((triisopropylsilyl)oxy)tetrahydrofuran-2-yl)-3-oxopropan-2-yl)carbamate
  参考文献：
  名称：

  Catalytic Asymmetric Total Synthesis of (+)-Caprazol

  摘要：

  Catalytic asymmetric total synthesis of caprazol, a lipo-nucleoside antibiotic, has been accomplished employing two of the stereoselective C-C bond forming reactions as key transformations. The stereochemistries of the β-hydroxy-α-aminoester moiety at the juncture of the uridine part and diazepanone part, and of the β-hydroxy-α-amino acid moiety embedded in the diazepanone system, were constructed using a diastereoselective isocyanoacetate aldol reaction (dr = 88:12) and an enantioselective anti-nitroaldol reaction catalyzed by a Nd/Na-chiral amide ligand (dr = 12:1, 95% ee), respectively.

  DOI：

  10.1021/ol501397b
• 作为产物：
  描述：

  (2S,3S)-methyl 3-(((3aR,4S,6R,6aR)-6-(azidomethyl)-2,2-diethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)-2-(((benzyloxy)carbonyl)amino)-3-((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-bis((triisopropylsilyl)oxy)tetrahydrofuran-2-yl)propanoate 在 三苯基膦 、 lithium iodide 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 反应 43.0h， 生成 (2S,3S)-2-(((benzyloxy)carbonyl)amino)-3-(((3aR,4S,6R,6aR)-6-(((tert-butoxycarbonyl)amino)methyl)-2,2-diethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)-3-((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-bis((triisopropylsilyl)oxy)tetrahydrofuran-2-yl)propanoic acid
  参考文献：
  名称：

  Catalytic Asymmetric Total Synthesis of (+)-Caprazol

  摘要：

  Catalytic asymmetric total synthesis of caprazol, a lipo-nucleoside antibiotic, has been accomplished employing two of the stereoselective C-C bond forming reactions as key transformations. The stereochemistries of the β-hydroxy-α-aminoester moiety at the juncture of the uridine part and diazepanone part, and of the β-hydroxy-α-amino acid moiety embedded in the diazepanone system, were constructed using a diastereoselective isocyanoacetate aldol reaction (dr = 88:12) and an enantioselective anti-nitroaldol reaction catalyzed by a Nd/Na-chiral amide ligand (dr = 12:1, 95% ee), respectively.

  DOI：

  10.1021/ol501397b