methyl (3S,4R,5R)-4-(N-tert-butoxycarbonyl-N-methylamino)-3,5-dihydroxyhexanoate | 1231183-99-5

• 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 (3S,4R,5R)-4-(N-tert-butoxycarbonyl-N-methylamino)-3,5-dihydroxyhexanoate
• 英文别名: methyl (3S,4R,5R)-3,5-dihydroxy-4-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]hexanoate
• CAS: 1231183-99-5
• 化学式: C₁₃H₂₅NO₆
• 分子量: 291.345
• InChiKey: AXXOIUNDEJMANM-WCABBAIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  96.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (3S,4R,5R)-4-(N-tert-butoxycarbonyl-N-methylamino)-3,5-dihydroxyhexanoate 在 camphorsulfonic acid 作用下， 以 苯 为溶剂， 反应 36.0h， 以68%的产率得到((2R,3R,4S)-4-hydroxy-2-methyl-6-oxotetrahydropyran-3-yl)-N-methylcarbamic acid tert-butyl ester
  参考文献：
  名称：

  Total synthesis of (+) methyl β-d-vicenisaminide

  摘要：

  The total synthesis of methyl beta-D-vicenisaminide 1 has been achieved. In this approach, the synthesis of enantiomerically pure methyl (4R,5S)- and (4S,5R)-4-azido-5-hydroxy-2(E)-hexenoates 2 was established by enzymatic resolution of (+/-)-anti-5-acetoxy -4-azido-2(E)-hexenoate 4. Another stereogenic center was introduced by base-catalyzed intramolecular conjugate addition of a hemiacetal-derived alkoxide nucleophile obtained by the reaction of methyl (4S,5R)-N-4-tert-butoxycarbonyl-N-methylamino-5-hydroxyl-2(E)-hexenoate 8 and benzaldehyde in the presence of a base. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.02.014
• 作为产物：
  描述：

  methyl [(4S,5R,6R)-5-(N-tert-butoxycarbonyl-N-methylamino)-6-methyl-2-phenyl[1,3]dioxan-4-yl]acetate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以78%的产率得到methyl (3S,4R,5R)-4-(N-tert-butoxycarbonyl-N-methylamino)-3,5-dihydroxyhexanoate
  参考文献：
  名称：

  Total synthesis of (+) methyl β-d-vicenisaminide

  摘要：

  The total synthesis of methyl beta-D-vicenisaminide 1 has been achieved. In this approach, the synthesis of enantiomerically pure methyl (4R,5S)- and (4S,5R)-4-azido-5-hydroxy-2(E)-hexenoates 2 was established by enzymatic resolution of (+/-)-anti-5-acetoxy -4-azido-2(E)-hexenoate 4. Another stereogenic center was introduced by base-catalyzed intramolecular conjugate addition of a hemiacetal-derived alkoxide nucleophile obtained by the reaction of methyl (4S,5R)-N-4-tert-butoxycarbonyl-N-methylamino-5-hydroxyl-2(E)-hexenoate 8 and benzaldehyde in the presence of a base. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.02.014