tert-butyl [(2S,3S,4R)-3,4-dihydroxy-1-(triisopropylsilyloxy)octadecan-2-yl]carbamate | 1226980-83-1

• 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: tert-butyl [(2S,3S,4R)-3,4-dihydroxy-1-(triisopropylsilyloxy)octadecan-2-yl]carbamate
• 英文别名: tert-butyl N-[(2S,3S,4R)-3,4-dihydroxy-1-tri(propan-2-yl)silyloxyoctadecan-2-yl]carbamate
• CAS: 1226980-83-1
• 化学式: C₃₂H₆₇NO₅Si
• 分子量: 573.973
• InChiKey: XADHILSWGYGALT-JBOQNHBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.88
• 重原子数：
  39
• 可旋转键数：
  24
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  88
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  原乙酸三甲酯 、 tert-butyl [(2S,3S,4R)-3,4-dihydroxy-1-(triisopropylsilyloxy)octadecan-2-yl]carbamate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到(R)-1-{(4S,5R)-2-oxo-4-[(triisopropylsilyloxy)methyl]oxazolidin-5-yl}pentadecyl acetate
  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
• 作为产物：
  描述：

  三异丙基氯硅烷 、 N-叔-丁基氧羰基-D-核-植物鞘氨醇 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到tert-butyl [(2S,3S,4R)-3,4-dihydroxy-1-(triisopropylsilyloxy)octadecan-2-yl]carbamate
  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.