phenyl 2-O-benzoyl-3,4-di-O-benzyl-1-thio-α-D-mannopyranoside | 1309789-70-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2-O-benzoyl-3,4-di-O-benzyl-1-thio-α-D-mannopyranoside
• 英文别名: [(2R,3S,4S,5R,6R)-6-(hydroxymethyl)-4,5-bis(phenylmethoxy)-2-phenylsulfanyloxan-3-yl] benzoate
• CAS: 1309789-70-5
• 化学式: C₃₃H₃₂O₆S
• 分子量: 556.679
• InChiKey: QTIQDQVNHXQOSN-HVXHYHBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  99.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  phenyl 2-O-benzoyl-3,4-di-O-benzyl-1-thio-α-D-mannopyranoside 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸酐 、 二苯基亚砜 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.08h， 生成 1-O-allyl-2-O-benzoyl-6-O-(2-O-benzoyl-3,4-di-O-benzyl-6-O-triisopropylsilyl-α-D-mannopyranosyl)-3,4,5-tri-O-benzyl-D-myo-inositol
  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 4,6-O-benzylidene-1-thio-α-D-mannopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 硼烷四氢呋喃络合物 、 二正丁基氧化锡 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.0h， 生成 phenyl 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

• Dissection of the effects that govern thioglucoside and thiomannoside reactivity
  作者：Mads Heuckendorff、Lulu Teressa Poulsen、Christinne Hedberg、Henrik H. Jensen

  DOI：10.1039/c7ob02968c

  日期：——

  Neighboring group effects were investigated in gluco- and manno-configured thioglycosides under NIS/TfOH activation. Donors possessing a 2-O-benzoyl group that are capable (1,2-trans) and incapable (1,2-cis) of exerting nucleophilic push were compared with donors possessing a participatory neutral 2-O-benzyl group. By using competition experiments between sets of glycosyl donors the direct effect of

  在NIS / TfOH活化下，在葡萄糖和甘露聚糖配置的硫糖苷中研究了相邻基团的作用。将具有2- O-苯甲酰基的施主与具有参与性中性2- O-苄基的施主进行比较，所述施主具有能够（1,2-反式）和不能（1,2-顺式）发挥亲核作用。通过使用糖基供体组之间的竞争实验，邻近基团参与的直接效应和2- O的电子吸收效应-苯甲酰基可被分离。该研究使人们深入了解了1和2位的立体化学，以及糖苷配基的性质（Ph或Et）如何对糖基供体的反应性产生显着影响。
• 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.