1-O-(β-D-psicofuranosyl)-N-stearoyl-D-erythro-sphingosine | 1146306-95-7

• 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: 1-O-(β-D-psicofuranosyl)-N-stearoyl-D-erythro-sphingosine
• 英文别名: N-[(E,2S,3R)-1-[(2R,3R,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxyoctadec-4-en-2-yl]octadecanamide
• CAS: 1146306-95-7
• 化学式: C₄₂H₈₁NO₈
• 分子量: 728.107
• InChiKey: IDLLHUYCXJAQJB-BIKCMIBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.7
• 重原子数：
  51
• 可旋转键数：
  36
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  149
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3-O-benzoyl-1-O-(1,6-di-O-benzoy-.β-D-psicofuranosyl)-N-stearoyl-D-erythro-sphingosine 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以90%的产率得到1-O-(β-D-psicofuranosyl)-N-stearoyl-D-erythro-sphingosine
  参考文献：
  名称：

  Stereoselective β-D-Psicofuranosylation and Synthesis of β-D-Psicofuranosylceramide

  摘要：

  Psicofurarlosylations of alcohols and phenol 3a-e with benzyl D-psicosyl phthalate 2 occurred on the beta-face to give beta-D-psicoside 4a-e in excellent yields. The reaction of ceramide 5 with 2 and deprotections of acetonide and three benzoates of the resulting glycoside afforded beta-D-psicosylceramide 1.

  DOI：

  10.3987/com-08-s(f)115

文献信息

• Stereoselective β-D-Psicofuranosylation and Synthesis of β-D-Psicofuranosylceramide
  作者：Jun'ichi Uenishi、Atsushi Ueda

  DOI：10.3987/com-08-s(f)115

  日期：——

  Psicofurarlosylations of alcohols and phenol 3a-e with benzyl D-psicosyl phthalate 2 occurred on the beta-face to give beta-D-psicoside 4a-e in excellent yields. The reaction of ceramide 5 with 2 and deprotections of acetonide and three benzoates of the resulting glycoside afforded beta-D-psicosylceramide 1.