phenyl (2-O-(2-azidomethylbenzoyl)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-2-O-benzoyl-3,4-di-O-benzyl-1-thio-α-D-mannopyranoside | 1309789-74-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl (2-O-(2-azidomethylbenzoyl)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-2-O-benzoyl-3,4-di-O-benzyl-1-thio-α-D-mannopyranoside
• 英文别名: [(2S,3S,4S,5R,6R)-2-[[(2R,3R,4S,5S,6R)-5-benzoyloxy-3,4-bis(phenylmethoxy)-6-phenylsulfanyloxan-2-yl]methoxy]-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] 2-(azidomethyl)benzoate
• CAS: 1309789-74-9
• 化学式: C₆₈H₆₅N₃O₁₂S
• 分子量: 1148.34
• InChiKey: OORIABOAURBZLX-GGCLEVMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.1
• 重原子数：
  84
• 可旋转键数：
  29
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  166
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  phenyl (2-O-(2-azidomethylbenzoyl)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-2-O-benzoyl-3,4-di-O-benzyl-1-thio-α-D-mannopyranoside 在 三丁基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以83%的产率得到phenyl (3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-2-O-benzoyl-3,4-di-O-benzyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Chemical Synthesis and Immunosuppressive Activity of Dipalmitoyl Phosphatidylinositol Hexamannoside

  摘要：

  Phosphatidylinositol mannosides (PIMs) isolated from mycobacteria have been identified as an important class of phosphoglycolipids with significant immune-modulating properties. We present here the synthesis of dipalmitoyl phosphatidylinositol hexamannoside (PIM6) 1 and the first reported functional biology of a synthetic PIM6. Key steps in the synthetic protocol included the selective glycosylation of an inositol 2,6-diol with a suitably protected mannosyl donor and construction of the glycan core utilizing a [3 + 4] thio-glycosylation strategy. The target 1 was purified by reverse phase chromatography and characterized by standard spectroscopic methods, HPLC, and chemical modification by deacylation to dPIM(6). The H-1 NMR spectrum of synthetic dPIM(6) obtained from 1 matched that of dPIM(6) obtained from nature. PIM6 (1) exhibited dendritic cell-dependent suppression of CD8(+) T cell expansion in a human mixed lymphocyte reaction consistent with the well established immunosuppressive activity of whole mycobacteria.

  DOI：

  10.1021/jo200588u
• 作为产物：
  描述：

  phenyl 2-O-benzoyl-3,4-di-O-benzyl-1-thio-α-D-mannopyranoside 、 2-O-(2-azidomethylbenzoyl)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙醚 为溶剂， 反应 0.5h， 以94%的产率得到phenyl (2-O-(2-azidomethylbenzoyl)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-2-O-benzoyl-3,4-di-O-benzyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Chemical Synthesis and Immunosuppressive Activity of Dipalmitoyl Phosphatidylinositol Hexamannoside

  摘要：

  Phosphatidylinositol mannosides (PIMs) isolated from mycobacteria have been identified as an important class of phosphoglycolipids with significant immune-modulating properties. We present here the synthesis of dipalmitoyl phosphatidylinositol hexamannoside (PIM6) 1 and the first reported functional biology of a synthetic PIM6. Key steps in the synthetic protocol included the selective glycosylation of an inositol 2,6-diol with a suitably protected mannosyl donor and construction of the glycan core utilizing a [3 + 4] thio-glycosylation strategy. The target 1 was purified by reverse phase chromatography and characterized by standard spectroscopic methods, HPLC, and chemical modification by deacylation to dPIM(6). The H-1 NMR spectrum of synthetic dPIM(6) obtained from 1 matched that of dPIM(6) obtained from nature. PIM6 (1) exhibited dendritic cell-dependent suppression of CD8(+) T cell expansion in a human mixed lymphocyte reaction consistent with the well established immunosuppressive activity of whole mycobacteria.

  DOI：

  10.1021/jo200588u

文献信息

• Chemical Synthesis and Immunosuppressive Activity of Dipalmitoyl Phosphatidylinositol Hexamannoside
  作者：Gary D. Ainge、Benjamin J. Compton、Colin M. Hayman、William John Martin、Steven M. Toms、David S. Larsen、Jacquie L. Harper、Gavin F. Painter

  DOI：10.1021/jo200588u

  日期：2011.6.17

  Phosphatidylinositol mannosides (PIMs) isolated from mycobacteria have been identified as an important class of phosphoglycolipids with significant immune-modulating properties. We present here the synthesis of dipalmitoyl phosphatidylinositol hexamannoside (PIM6) 1 and the first reported functional biology of a synthetic PIM6. Key steps in the synthetic protocol included the selective glycosylation of an inositol 2,6-diol with a suitably protected mannosyl donor and construction of the glycan core utilizing a [3 + 4] thio-glycosylation strategy. The target 1 was purified by reverse phase chromatography and characterized by standard spectroscopic methods, HPLC, and chemical modification by deacylation to dPIM(6). The H-1 NMR spectrum of synthetic dPIM(6) obtained from 1 matched that of dPIM(6) obtained from nature. PIM6 (1) exhibited dendritic cell-dependent suppression of CD8(+) T cell expansion in a human mixed lymphocyte reaction consistent with the well established immunosuppressive activity of whole mycobacteria.