Methyl (4R,5S)-5-methyl-4,5-dihydro-1,3-oxazole-4-carboxylate | 53216-07-2

• 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 (4R,5S)-5-methyl-4,5-dihydro-1,3-oxazole-4-carboxylate
• 英文别名: methyl (4R,5S)-5-methyl-4,5-dihydro-1,3-oxazole-4-carboxylate
• CAS: 53216-07-2；53229-11-1；58861-76-0；62211-72-7；62211-73-8；104320-71-0；118916-74-8；118916-78-2
• 化学式: C₆H₉NO₃
• 分子量: 143.142
• InChiKey: RAAGHFMDHMDDNX-CRCLSJGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl (4R,5S)-5-methyl-4,5-dihydro-1,3-oxazole-4-carboxylate 在 三乙基硅烷 、 三氟乙酸 、 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 40.0h， 生成 N-methyl-D-threonine
  参考文献：
  名称：

  Coibamide A, a Potent Antiproliferative Cyclic Depsipeptide from the Panamanian Marine Cyanobacterium Leptolyngbya sp.

  摘要：

  Coibamide A (1) is a new, potent antiproliferative depsipeptide which was isolated from a marine Leptolyngbya cyanobacterium collected from the Coiba National Park, Panama. The planar structure of I was elucidated by a combination of NMR spectroscopy and mass spectrometry. Exhaustive 1 D and 2D NMR spectroscopy included natural abundance (15)N and variable temperature experiments; mass spectrometry included TOF-ESI-MS(n) and FT-MS(n) experiments, Chemical degradation followed by chiral HPLC- and GC-MS analyses was used to assign the absolute configuration of 1. This highly methylated cyclized depsipeptide exhibited an unprecedented selectivity profile in the NCl 60 cancer cell line panel and appears to act via a novel mechanism.

  DOI：

  10.1021/ja801383f
• 作为产物：
  描述：

  聚合甲醛 、 Z-苏氨酸甲酯 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 Methyl (4R,5S)-5-methyl-4,5-dihydro-1,3-oxazole-4-carboxylate
  参考文献：
  名称：

  Coibamide A, a Potent Antiproliferative Cyclic Depsipeptide from the Panamanian Marine Cyanobacterium Leptolyngbya sp.

  摘要：

  Coibamide A (1) is a new, potent antiproliferative depsipeptide which was isolated from a marine Leptolyngbya cyanobacterium collected from the Coiba National Park, Panama. The planar structure of I was elucidated by a combination of NMR spectroscopy and mass spectrometry. Exhaustive 1 D and 2D NMR spectroscopy included natural abundance (15)N and variable temperature experiments; mass spectrometry included TOF-ESI-MS(n) and FT-MS(n) experiments, Chemical degradation followed by chiral HPLC- and GC-MS analyses was used to assign the absolute configuration of 1. This highly methylated cyclized depsipeptide exhibited an unprecedented selectivity profile in the NCl 60 cancer cell line panel and appears to act via a novel mechanism.

  DOI：

  10.1021/ja801383f

文献信息

• Asymmetric synthesis catalyzed by chiral ferrocenylphosphine transition metal complexes. 10 gold(i)-catalyzed asymmetric aldol reaction of isocyanoacetate
  作者：Tamio Hayashi、Masaya Sawamura、Yoshihiko Ito

  DOI：10.1016/s0040-4020(01)88870-0

  日期：1992.1

  Optically active ferrocenylbisphosphine ligands containing 2-(dialkylamino)ethylamino group on the ferrocenylmethyl position have been prepared and used for the gold(I)-catalyzed asymmetric aldol reaction of isocyanoacetate with aldehydes. Six-membered ring amines, such as morpholino or piperidino group, at the terminal of the side chain were most stereoselective to give optically active trans-4-

  制备了在二茂铁基甲基位置上含有2-（二烷基氨基）乙基氨基的旋光二茂铁基双膦配体，并将其用于金（I）催化的异氰基乙酸酯与醛的不对称醛醇缩合反应。侧链末端的六元环胺（例如吗啉代或哌啶子基）具有最高的立体选择性，可生成具有高对映体的光学活性反式-4-甲氧羰基-5-烷基-2-恶唑啉（ee最高可达97％） -和非对映选择性的定量收率。
• Asymmetric aldol reaction of α-isocyanoacetamides with aldehydes catalyzed by a chiral ferrocenylphosphine-gold(I) complex
  作者：Yoshihiko Ito、Masaya Sawamura、Masaaki Kobayashi、Tamio Hayashi

  DOI：10.1016/s0040-4039(00)82336-9

  日期：1988.1

  Aldol reaction of ,-dialkyl-α-isocyanoacetamides with primary alkyl aldehydes in the presence of 0.5–1 mol% of a chiral (aminoalkyl) ferrocenylphosphine-gold(I) catalyst proceeded with high enantio- and diastereoselectivity to give trans-5-alkyl-2-oxazoline-4-carboxamides of up to 98.6% ee, which were converted into optically active threo-β-hydroxyamino acids.

  在0.5-1 mol％手性（氨基烷基）二茂铁基膦-金（I）催化剂的存在下，-二烷基-α-异氰基乙酰胺与伯烷基醛的醛醇缩合反应以高对映体和非对映体选择性进行，得到反式-5-烷基最多将98.6％ee的-2-恶唑啉-4-羧酰胺转化为旋光的苏-β-羟氨基酸。