(2S,3S,4R,5S)-5-azido-2,3,4-tris(benzyloxy)-6-((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yloxy)hexan-1-ol | 1325147-10-1

• 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,3S,4R,5S)-5-azido-2,3,4-tris(benzyloxy)-6-((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yloxy)hexan-1-ol
• 英文别名: (2S,3S,4R,5S)-5-azido-2,3,4-tris(phenylmethoxy)-6-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyhexan-1-ol
• CAS: 1325147-10-1
• 化学式: C₆₁H₆₅N₃O₁₀
• 分子量: 1000.2
• InChiKey: RVOUHTJZJWTSAR-CILANTDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  74
• 可旋转键数：
  30
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5S)-5-azido-2,3,4-tris(benzyloxy)-6-((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yloxy)hexan-1-ol 、 溴代十二烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.33h， 以77%的产率得到(2S,3R,4S,5S,6R)-2-((2S,3R,4S,5S)-2-azido-3,4,5-tris(benzyloxy)-6-(dodecyloxy)hexyloxy)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)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
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1→6)-2,3,4-tri-O-benzyl-D-glucopyranose 在 吡啶 、 甲醇 、 sodium tetrahydroborate 、 偶氮二甲酸二异丙酯 、 叠氮磷酸二苯酯 、 sodium methylate 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 58.0h， 生成 (2S,3S,4R,5S)-5-azido-2,3,4-tris(benzyloxy)-6-((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yloxy)hexan-1-ol
  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

文献信息

• The Total Synthesis of Immunostimulant α-Galactosylceramides from Naturally Configured α-Galactoside Raffinose
  作者：Zhenxing Zhang、Wei Zhao、Bin Wang、Chengfeng Xia、Wenpeng Zhang、Peng George Wang

  DOI：10.1021/ol201695n

  日期：2011.9.2

  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.