ethyl 2-((2R,3S,5S,6S)-6-(3-(benzyloxy)propyl)-3-hydroxy-5-methyltetrahydro-2H-pyran-2-yl)acetate | 1185202-64-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-((2R,3S,5S,6S)-6-(3-(benzyloxy)propyl)-3-hydroxy-5-methyltetrahydro-2H-pyran-2-yl)acetate
• 英文别名: ethyl 2-[(2R,3S,5S,6S)-3-hydroxy-5-methyl-6-(3-phenylmethoxypropyl)oxan-2-yl]acetate
• CAS: 1185202-64-5
• 化学式: C₂₀H₃₀O₅
• 分子量: 350.455
• InChiKey: ZROPIQHQJZVRSO-DSLXNQLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-((2R,3S,5S,6S)-6-(3-(benzyloxy)propyl)-3-hydroxy-5-methyltetrahydro-2H-pyran-2-yl)acetate 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Total Synthesis of Brevisamide

  摘要：

  The second total synthesis of Brevisamide, a marine cyclic ether alkaloid from Karenia brevis, is reported. This streamlined synthesis proceeds in 21 steps, 14 steps longest linear sequence, in 5.2% overall yield and features a key Sml(2) reductive cyclization step to access the tetrasubstituted pyran core.

  DOI：

  10.1021/ol9015755
• 作为产物：
  描述：

  4-苯基甲氧基-丁醛 在 2,6-二甲基吡啶 、 20 % Pd(OH)2/C 、 四丁基氟化铵 、 氢气 、 四氯化钛 、 二异丁基氢化铝 、 三乙胺 、 亚硝基苯 、 D-脯氨酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 二甲基亚砜 、 苯 为溶剂， 反应 3.09h， 生成 ethyl 2-((2R,3S,5S,6S)-6-(3-(benzyloxy)propyl)-3-hydroxy-5-methyltetrahydro-2H-pyran-2-yl)acetate
  参考文献：
  名称：

  Palladium Hydroxide Catalyzed Isomerization of Primary Allylic Alcohols to Aldehydes: Application to the Formal Synthesis of (−)-Brevisamide

  摘要：

  The Pd-catalyzed isomerization of primary allylic alcohols into the corresponding saturated aldehydes has been achieved at room temperature for the first time in good to excellent yields under mild conditions. The functional group compatibility in this reaction is studied, and this new methodology has been successfully applied in the synthesis of a C5-C13 tetrahydropyran ring system of (-)-brevisamide in seven steps.

  DOI：

  10.1021/ol102658d

文献信息

• Palladium Hydroxide Catalyzed Isomerization of Primary Allylic Alcohols to Aldehydes: Application to the Formal Synthesis of (−)-Brevisamide
  作者：Gowravaram Sabitha、Sambit Nayak、M. Bhikshapathi、J. S. Yadav

  DOI：10.1021/ol102658d

  日期：2011.2.4

  The Pd-catalyzed isomerization of primary allylic alcohols into the corresponding saturated aldehydes has been achieved at room temperature for the first time in good to excellent yields under mild conditions. The functional group compatibility in this reaction is studied, and this new methodology has been successfully applied in the synthesis of a C5-C13 tetrahydropyran ring system of (-)-brevisamide in seven steps.
• Total Synthesis of Brevisamide
  作者：Olugbeminiyi O. Fadeyi、Craig W. Lindsley

  DOI：10.1021/ol9015755

  日期：2009.9.3

  The second total synthesis of Brevisamide, a marine cyclic ether alkaloid from Karenia brevis, is reported. This streamlined synthesis proceeds in 21 steps, 14 steps longest linear sequence, in 5.2% overall yield and features a key Sml(2) reductive cyclization step to access the tetrasubstituted pyran core.