(2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-((2R,3R,4R,5S)-3,4,5-tris(benzyloxy)-2,6-bis(decyloxy)hexyloxy)tetrahydro-2H-pyran | 1325147-15-6

• 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: (2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-((2R,3R,4R,5S)-3,4,5-tris(benzyloxy)-2,6-bis(decyloxy)hexyloxy)tetrahydro-2H-pyran
• CAS: 1325147-15-6
• 化学式: C₈₁H₁₀₆O₁₁
• 分子量: 1255.73
• InChiKey: RNCAVDUQWXWWQD-QXGNQLNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.14
• 重原子数：
  92.0
• 可旋转键数：
  49.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  101.53
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-((2R,3R,4R,5S)-3,4,5-tris(benzyloxy)-2,6-bis(decyloxy)hexyloxy)tetrahydro-2H-pyran 在 10% palladium hydroxide on charcoal 、 氢气 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 5.0h， 以76%的产率得到(2S,3R,4S,5S,6R)-2-((2R,3S,4R,5S)-2,6-bis(decyloxy)-3,4,5-trihydroxyhexyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
  参考文献：
  名称：

  The Total Synthesis of Immunostimulant α-Galactosylceramides from Naturally Configured α-Galactoside Raffinose

  摘要：

  The total synthesis of absolute anomeric confirmation alpha-galactosylceramide analogues from raffinose is described. Using the naturally occurring alpha-galactoside raffinose as the starting material, the easily maneuverable protocol without glycosylation reactions ensured the critical alpha-linkage in the product and simplified the synthetic procedures. The immunostimulatory activities of the new alpha-galactosylceramides were validated by both in vitro and in vivo NKT cell stimulation assays.

  DOI：

  10.1021/ol201695n
• 作为产物：
  描述：

  癸基溴 、 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-D-glucitol 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以77%的产率得到(2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-((2R,3R,4R,5S)-3,4,5-tris(benzyloxy)-2,6-bis(decyloxy)hexyloxy)tetrahydro-2H-pyran
  参考文献：
  名称：

  The Total Synthesis of Immunostimulant α-Galactosylceramides from Naturally Configured α-Galactoside Raffinose

  摘要：

  The total synthesis of absolute anomeric confirmation alpha-galactosylceramide analogues from raffinose is described. Using the naturally occurring alpha-galactoside raffinose as the starting material, the easily maneuverable protocol without glycosylation reactions ensured the critical alpha-linkage in the product and simplified the synthetic procedures. The immunostimulatory activities of the new alpha-galactosylceramides were validated by both in vitro and in vivo NKT cell stimulation assays.

  DOI：

  10.1021/ol201695n