tert-butyl N-[(2S,3R)-3-[tert-butyl(diphenyl)silyl]oxy-1-[(2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxypent-4-en-2-yl]carbamate | 1020409-66-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: tert-butyl N-[(2S,3R)-3-[tert-butyl(diphenyl)silyl]oxy-1-[(2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxypent-4-en-2-yl]carbamate
• CAS: 1020409-66-8
• 化学式: C₆₀H₇₁NO₉Si
• 分子量: 978.311
• InChiKey: OMDXWRHIJLQBKS-HJCIINMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.73
• 重原子数：
  71
• 可旋转键数：
  26
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  tert-butyl (2S,3R)-3-(tert-butyldiphenylsilyloxy)-1-hydroxypent-4-en-2-ylcarbamate 、 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl fluoride 在 silver perchlorate 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.5h， 以30%的产率得到(2S,3R)-2-(tert-butyloxycarbonylamino)-3-O-(tert-butyldiphenylsilyl)-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)pent-4-ene
  参考文献：
  名称：

  Focus on the Controversial Activation of Human iNKT Cells by 4-Deoxy Analogue of KRN7000

  摘要：

  4-Deoxy-alpha-GalCer analogues are considered weaker agonists than KRN7000 for the stimulation of human iNKT cells, but this remains strongly debated. In this work, we described a strategy toward 4-deoxy-alpha-GalCers with, as a key step, a metathesis reaction allowing sphingosine modifications from a single ethylenic alpha-galactoside precursor. The 4-deoxy-KRN7000 derivative 2, described here, induced potent cytokinic responses, comparable to those of KRN7000, both from human iNKT cells in vitro and from their murine counterpart in vivo.

  DOI：

  10.1021/jm900290r