(4R,5S)-4-(acetyloxymethyl)-3-(4-methylphenyl)sulfonyl-2-oxo-5-pentyl-1,3-oxazolidine-4-carboxylic acid | 1214788-59-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4R,5S)-4-(acetyloxymethyl)-3-(4-methylphenyl)sulfonyl-2-oxo-5-pentyl-1,3-oxazolidine-4-carboxylic acid
• CAS: 1214788-59-6
• 化学式: C₁₉H₂₅NO₈S
• 分子量: 427.475
• InChiKey: KQTXNYQLNCNDSA-QFBILLFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  136
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  在 ruthenium trichloride 、 sodium periodate 、 水 作用下， 以 四氯化碳 、 乙腈 为溶剂， 以45%的产率得到(4R,5S)-4-(acetyloxymethyl)-3-(4-methylphenyl)sulfonyl-2-oxo-5-pentyl-1,3-oxazolidine-4-carboxylic acid
  参考文献：
  名称：

  Regio- and stereoselective microwave-assisted synthesis of 5-alkyl-4-alkenyl-4-phenyl-1,3-oxazolidin-2-ones

  摘要：

  Chiral symmetrical alk-2-yne-1,4-diols have been stereoselectively transformed into 5-alkyl-4-alkenyl-4-phenyl-1,3-oxazolidin-2-ones, which are precursors of quaternary alpha-amino beta-hydroxy acids. The key step was the cyclization of the bis(tosylcarbamates) of 2-phenylalk-2-yne-1,4-diols, easily obtained from the starting chiral diols. These cyclizations were accomplished with complete regioselectivity and up to 92:8 dr in the presence of catalytic amounts of Ni(0) or Pd (II) derivatives under microwave heating. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.12.036