tert-butyl 2-((4S,5R)-4,5-dimethyl-4-hydroxy-5-methoxy-2-oxooxazolidin-3-yl)acrylate | 1533407-52-1

• 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 2-((4S,5R)-4,5-dimethyl-4-hydroxy-5-methoxy-2-oxooxazolidin-3-yl)acrylate
• 英文别名: tert-butyl 2-[(4S,5R)-4-hydroxy-5-methoxy-4,5-dimethyl-2-oxo-1,3-oxazolidin-3-yl]prop-2-enoate
• CAS: 1533407-52-1
• 化学式: C₁₃H₂₁NO₆
• 分子量: 287.313
• InChiKey: GLZWOGXSVQYUTQ-QWHCGFSZSA-N

物化性质

• 熔点：
  85-87 °C
• 沸点：
  363.9±52.0 °C(predicted)
• 密度：
  1.20±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 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：

  tert-butyl 2-((4S,5R)-4,5-dimethyl-4-hydroxy-5-methoxy-2-oxooxazolidin-3-yl)acrylate 、 1-thio-2-N-acetylamino-3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-galactopyranose 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以86%的产率得到tert-butyl (2S)-2-((4S,5R)-4,5-dimethyl-4-hydroxy-5-methoxy-2-oxooxazolidin-3-yl)-3-(tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactosylthio)propanoate
  参考文献：
  名称：

  S-Michael Additions to Chiral Dehydroalanines as an Entry to Glycosylated Cysteines and a Sulfa-Tn Antigen Mimic

  摘要：

  Stereoselective sulfa-Michael addition of appropriately protected thiocarbohydrates to chiral dehydroalanines has been developed as a key step in the synthesis of biologically important cysteine derivatives, such as S-(beta-D-glucopyranosyl)-D-cysteine, which has not been synthesized to date, and S-(2-acetamido-2-deoxy-alpha-D-galactopyranosyl)-L-cysteine, which could be considered as a mimic of Tn antigen. The corresponding diamide derivative was also synthesized and analyzed from a conformational viewpoint, and its bound state with a lectin was studied.

  DOI：

  10.1021/ja411522f
• 作为产物：
  描述：

  tert-butyl (3S,7R,7aS)-7-methoxy-7,7a-dimethyl-5-oxotetrahydro-5H-oxazolo[4,3-b]oxazole-3-carboxylate 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以95%的产率得到tert-butyl 2-((4S,5R)-4,5-dimethyl-4-hydroxy-5-methoxy-2-oxooxazolidin-3-yl)acrylate
  参考文献：
  名称：

  S-Michael Additions to Chiral Dehydroalanines as an Entry to Glycosylated Cysteines and a Sulfa-Tn Antigen Mimic

  摘要：

  Stereoselective sulfa-Michael addition of appropriately protected thiocarbohydrates to chiral dehydroalanines has been developed as a key step in the synthesis of biologically important cysteine derivatives, such as S-(beta-D-glucopyranosyl)-D-cysteine, which has not been synthesized to date, and S-(2-acetamido-2-deoxy-alpha-D-galactopyranosyl)-L-cysteine, which could be considered as a mimic of Tn antigen. The corresponding diamide derivative was also synthesized and analyzed from a conformational viewpoint, and its bound state with a lectin was studied.

  DOI：

  10.1021/ja411522f