tert-butyl (4S)-4-[(E,1R)-1-(methoxymethoxy)hexadec-2-enyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate | 246245-46-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: tert-butyl (4S)-4-[(E,1R)-1-(methoxymethoxy)hexadec-2-enyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 246245-46-5
• 化学式: C₂₈H₅₃NO₅
• 分子量: 483.733
• InChiKey: YWOFLYFQVVBCDQ-LJLZLVTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  34
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (4S)-4-[(E,1R)-1-(methoxymethoxy)hexadec-2-enyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 在 水 、 溶剂黄146 作用下， 以90%的产率得到tert-butyl (2S,3R,4E)-1-hydroxy-3-(methoxymethoxy)octadec-4-en-2-yl-carbamate
  参考文献：
  名称：

  A short enantiodivergent synthesis of d-erythro and l-threo sphingosine

  摘要：

  A new, short (6 steps) and efficient enantiodivergent route to both D-erythro and L threo-sphingosine I and II is disclosed. The high diastereoselection (100% de) reached in the creation of the C-3 stereocenter relies on the use of a sulfoxide as chiral controlling agent in the reduction of the common precursor beta-keto sulfoxide 3. The desired E-alkene of sphingosines has been constructed by the Schlosser modification of the Wittig reaction between aldehyde 8 and the phosphoniun salt 9. The reported methodology can easily be extended to the synthesis of a large number of optically pure syn and anti amino alcohols starting from commercially available amino acids. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01112-0
• 作为产物：
  描述：

  (S)-(-)-3-BOC-4-甲氧羰基-2,2-二甲基-1,3-恶唑烷 在 2,3,5-三甲基吡啶 、 草酰氯 、 sodium hydride 、 二异丁基氢化铝 、 二甲基亚砜 、 苯基锂 、 三乙胺 、 三氟乙酸酐 、 lithium bromide 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 、 乙腈 为溶剂， 反应 0.5h， 生成 tert-butyl (4S)-4-[(E,1R)-1-(methoxymethoxy)hexadec-2-enyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  A short enantiodivergent synthesis of d-erythro and l-threo sphingosine

  摘要：

  A new, short (6 steps) and efficient enantiodivergent route to both D-erythro and L threo-sphingosine I and II is disclosed. The high diastereoselection (100% de) reached in the creation of the C-3 stereocenter relies on the use of a sulfoxide as chiral controlling agent in the reduction of the common precursor beta-keto sulfoxide 3. The desired E-alkene of sphingosines has been constructed by the Schlosser modification of the Wittig reaction between aldehyde 8 and the phosphoniun salt 9. The reported methodology can easily be extended to the synthesis of a large number of optically pure syn and anti amino alcohols starting from commercially available amino acids. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01112-0

文献信息

• A short enantiodivergent synthesis of d-erythro and l-threo sphingosine
  作者：Noureddine Khiar、Kamaljit Singh、Mercedes García、Manuel Martín-Lomas

  DOI：10.1016/s0040-4039(99)01112-0

  日期：1999.7

  A new, short (6 steps) and efficient enantiodivergent route to both D-erythro and L threo-sphingosine I and II is disclosed. The high diastereoselection (100% de) reached in the creation of the C-3 stereocenter relies on the use of a sulfoxide as chiral controlling agent in the reduction of the common precursor beta-keto sulfoxide 3. The desired E-alkene of sphingosines has been constructed by the Schlosser modification of the Wittig reaction between aldehyde 8 and the phosphoniun salt 9. The reported methodology can easily be extended to the synthesis of a large number of optically pure syn and anti amino alcohols starting from commercially available amino acids. (C) 1999 Elsevier Science Ltd. All rights reserved.