(S)-4-[(1S,2R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyhexadecyl]oxazolidin-2-one | 1226980-98-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (S)-4-[(1S,2R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyhexadecyl]oxazolidin-2-one
• 英文别名: (4S)-4-[(1S,2R)-2-[tert-butyl(diphenyl)silyl]oxy-1-hydroxyhexadecyl]-1,3-oxazolidin-2-one
• CAS: 1226980-98-8
• 化学式: C₃₅H₅₅NO₄Si
• 分子量: 581.912
• InChiKey: VHLWEVZXKJEGCN-DSPMFFIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.49
• 重原子数：
  41
• 可旋转键数：
  20
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-O-tert-butyldiphenylsilyl-1-N-tert-butyloxycarbonylphytosphingosine 在 potassium tert-butylate 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 以47%的产率得到(S)-4-[(1S,2R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyhexadecyl]oxazolidin-2-one
  参考文献：
  名称：

  Stereoselective Divergent Synthesis of Four Diastereomers of Pachastrissamine (Jaspine B)

  摘要：

  A divergent short synthesis of four diastereomers of pachastrissamine was achieved. Natural pachastrissamine was synthesized through bis-tosylation of the common intermediate and cyclization. 2-epi-Pachastrissamine was obtained by monotosylation and spontaneous cyclization of D-ribo-phytosphingosine derivative. By use of regio- and stereospecific ring-opening reaction of the orthoester assisted by a Bee group as a key step, 3-epi- and 2,3-epi-pachastrissamines were synthesized. The three stereogenic centers of all the diastereomers were constructed by using Garner's aldehyde as the sole chiral source.

  DOI：

  10.1021/jo1005284

文献信息

• Stereoselective Divergent Synthesis of Four Diastereomers of Pachastrissamine (Jaspine B)
  作者：Yuji Yoshimitsu、Shinsuke Inuki、Shinya Oishi、Nobutaka Fujii、Hiroaki Ohno

  DOI：10.1021/jo1005284

  日期：2010.6.4

  A divergent short synthesis of four diastereomers of pachastrissamine was achieved. Natural pachastrissamine was synthesized through bis-tosylation of the common intermediate and cyclization. 2-epi-Pachastrissamine was obtained by monotosylation and spontaneous cyclization of D-ribo-phytosphingosine derivative. By use of regio- and stereospecific ring-opening reaction of the orthoester assisted by a Bee group as a key step, 3-epi- and 2,3-epi-pachastrissamines were synthesized. The three stereogenic centers of all the diastereomers were constructed by using Garner's aldehyde as the sole chiral source.