(4S)-3-[(3R)-4-(2-ethyl-1,3-dioxolan-2-yl)-3-hydroxy-4-methylpentanoyl]-4-(methylethyl)-1,3-oxazolidin-2-one | 311761-32-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S)-3-[(3R)-4-(2-ethyl-1,3-dioxolan-2-yl)-3-hydroxy-4-methylpentanoyl]-4-(methylethyl)-1,3-oxazolidin-2-one
• 英文别名: (4S)-3-[(3R)-4-(2-ethyl-1,3-dioxolan-2-yl)-3-hydroxy-4-methylpentanoyl]-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 311761-32-7
• 化学式: C₁₇H₂₉NO₆
• 分子量: 343.42
• InChiKey: SZBUASCJBATDSW-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4S)-3-[(3R)-4-(2-ethyl-1,3-dioxolan-2-yl)-3-hydroxy-4-methylpentanoyl]-4-(methylethyl)-1,3-oxazolidin-2-one 在 lithium hydroxide 、 水 、 双氧水 、 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以76%的产率得到(3R)-3-hydroxy-4,4-dimethyl-5-oxoheptanoic acid
  参考文献：
  名称：

  An Unusual Reversal of Stereoselectivity in a Boron Mediated Aldol Reaction: Enantioselective Synthesis of the C1–C6 Segment of the Epothilones

  摘要：

  Enantioselective syntheses of differentially protected C-1-C-6 fragments, (3S)-3-hydroxy-4,4-dimethyl-5-oxoheptanoic acid 4, (5S)-7-[1,1-bis(mechylethyl)-2-methyl-1 -silapropoxy]-5-hydroxy-4,4-dimethylheptan-3-one 5 and (4S)-2-(2,2-dimethyl-1,3-dioxan-4-yl)-2-methylpentan-3-one 23, common to both epothilones A and B, are reported. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00708-0
• 作为产物：
  描述：

  3,3-dimethyl-4-oxohex-1-ene 在 4-甲基苯磺酸吡啶 、 臭氧 、 N,N-二异丙基乙胺 、 9-硼杂双环[3.3.1]壬基三氟甲磺酸酯 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 36.5h， 生成 (4S)-3-[(3R)-4-(2-ethyl-1,3-dioxolan-2-yl)-3-hydroxy-4-methylpentanoyl]-4-(methylethyl)-1,3-oxazolidin-2-one
  参考文献：
  名称：

  An Unusual Reversal of Stereoselectivity in a Boron Mediated Aldol Reaction: Enantioselective Synthesis of the C1–C6 Segment of the Epothilones

  摘要：

  Enantioselective syntheses of differentially protected C-1-C-6 fragments, (3S)-3-hydroxy-4,4-dimethyl-5-oxoheptanoic acid 4, (5S)-7-[1,1-bis(mechylethyl)-2-methyl-1 -silapropoxy]-5-hydroxy-4,4-dimethylheptan-3-one 5 and (4S)-2-(2,2-dimethyl-1,3-dioxan-4-yl)-2-methylpentan-3-one 23, common to both epothilones A and B, are reported. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00708-0

文献信息

• An Unusual Reversal of Stereoselectivity in a Boron Mediated Aldol Reaction: Enantioselective Synthesis of the C1–C6 Segment of the Epothilones
  作者：Bijoy Panicker、Jean M Karle、Mitchell A Avery

  DOI：10.1016/s0040-4020(00)00708-0

  日期：2000.9

  Enantioselective syntheses of differentially protected C-1-C-6 fragments, (3S)-3-hydroxy-4,4-dimethyl-5-oxoheptanoic acid 4, (5S)-7-[1,1-bis(mechylethyl)-2-methyl-1 -silapropoxy]-5-hydroxy-4,4-dimethylheptan-3-one 5 and (4S)-2-(2,2-dimethyl-1,3-dioxan-4-yl)-2-methylpentan-3-one 23, common to both epothilones A and B, are reported. (C) 2000 Elsevier Science Ltd. All rights reserved.