(2R)-3,3-dimethyl-2,4-bis[(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl)oxy]butanoic acid | 144762-89-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R)-3,3-dimethyl-2,4-bis[(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl)oxy]butanoic acid
• CAS: 144762-89-0
• 化学式: C₂₂H₃₈N₂O₈
• 分子量: 458.552
• InChiKey: ANSVZGUYVISQME-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R)-3,3-dimethyl-2,4-bis[(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl)oxy]butanoic acid 在 盐酸 作用下， 反应 12.0h， 生成 D-(-)-泛酰内酯
  参考文献：
  名称：

  Chiral α,ω-dioxy-carbanions from 1,3-propanediol and 1,4-butanediol by sparteine-assisted deprotonation. Enantioselective synthesis of 1,3- and 1,4-diols, (R)-pantolactone, and a cyclopropane.

  摘要：

  Prostereogenic mono- and dicarbamates of 1,3-propanediol and 1,4-butanediol are deprotonated by the sec-butyllithium/(-)-sparteine system with high enantiotopic differentiation. The electrophilic substitution of the intermediate chiral carbanions furnishes the title compounds with >95% ee.

  DOI：

  10.1016/s0040-4039(00)79083-6
• 作为产物：
  描述：

  二氧化碳 、 [2,2-Dimethyl-3-(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl)oxypropyl] 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate 在 仲丁基锂 、 鹰爪豆碱 作用下， 生成 (2R)-3,3-dimethyl-2,4-bis[(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl)oxy]butanoic acid
  参考文献：
  名称：

  Chiral α,ω-dioxy-carbanions from 1,3-propanediol and 1,4-butanediol by sparteine-assisted deprotonation. Enantioselective synthesis of 1,3- and 1,4-diols, (R)-pantolactone, and a cyclopropane.

  摘要：

  Prostereogenic mono- and dicarbamates of 1,3-propanediol and 1,4-butanediol are deprotonated by the sec-butyllithium/(-)-sparteine system with high enantiotopic differentiation. The electrophilic substitution of the intermediate chiral carbanions furnishes the title compounds with >95% ee.

  DOI：

  10.1016/s0040-4039(00)79083-6

文献信息

• Chiral α,ω-dioxy-carbanions from 1,3-propanediol and 1,4-butanediol by sparteine-assisted deprotonation. Enantioselective synthesis of 1,3- and 1,4-diols, (R)-pantolactone, and a cyclopropane.
  作者：Mario Paetow、Hartmut Ahrens、Dieter Hoppe

  DOI：10.1016/s0040-4039(00)79083-6

  日期：1992.9

  Prostereogenic mono- and dicarbamates of 1,3-propanediol and 1,4-butanediol are deprotonated by the sec-butyllithium/(-)-sparteine system with high enantiotopic differentiation. The electrophilic substitution of the intermediate chiral carbanions furnishes the title compounds with >95% ee.