2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl dimethyl phosphite | 148171-71-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl dimethyl phosphite
• 英文别名: (2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)dimethylphosphite；dimethyl [(2R,3S,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl] phosphite
• CAS: 148171-71-5
• 化学式: C₃₆H₄₁O₈P
• 分子量: 632.69
• InChiKey: NKFCEJUKCPDRQP-DQROVBKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  45
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl dimethyl phosphite 在 ammonium cerium(IV) nitrate 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 乙醚 、 水 、 乙腈 为溶剂， 反应 1.33h， 生成 3,4,5,6-tetra-O-benzyl-1-O-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)-D-myo-inositol
  参考文献：
  名称：

  磷脂酰肌醇甘露糖苷：合成和抑制过敏性气道疾病。

  摘要：

  先前已证明，分枝杆菌的磷脂酰肌醇甘露糖苷（PIM）提取物可抑制小鼠的过敏性气道炎症。为了帮助确定活性的结构要求，合成了PIM1（2）（1），PIM1（6）（2）和PIM2（3），并测试了它们在变应性哮喘小鼠模型中抑制细胞炎症的能力。合成的PIM在哮喘模型中均能有效抑制气道嗜酸性粒细胞增多，其中PIM1（6）最有效。观察到所监测的所有炎性细胞的抑制，表明细胞炎的普遍阻断。非甘露糖基化磷脂酰肌醇（PI）没有抑制作用，表明至少一个α-d-甘露聚糖基对活性是必需的。

  DOI：

  10.1016/j.bmc.2006.04.037
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 、 N,N-二异丙基亚膦酸二甲酯酰胺 在 4,5-二氯咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 1.75h， 生成 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl dimethyl phosphite
  参考文献：
  名称：

  [EN] SYNTHETIC MOLECULES HAVING IMMUNE ACTIVITY
  [FR] MOLECULES SYNTHETIQUES A IMMUNO-ACTIVITE

  摘要：

  本发明涉及具有类似于PIM（酰基甘油磷脂肌醇寡糖）活性的合成分子，用于治疗和预防炎症性或免疫细胞介导的疾病或紊乱。

  公开号：

  WO2005049631A1

文献信息

• Glycosylation using glycosyl phosphite as a glycosyl donor
  作者：Yutaka Watanabe、Chikara Nakamoto、Takashi Yamamoto、Shoichiro Ozaki

  DOI：10.1016/s0040-4020(01)89683-6

  日期：——

  Glycosylation using glycosyl phosphites as glycosyl donors in the presence of a Lewis acid such as ZnCl2 or ZnCl2-AgClO4 has afforded the glycosides including sialoglycosides in good yields.
• A PIM2 analogue suppresses allergic airway disease
  作者：Jacquie L. Harper、Colin M. Hayman、David S. Larsen、Gavin F. Painter、Gurmit Singh-Gill

  DOI：10.1016/j.bmc.2010.11.058

  日期：2011.1

  Two approaches for the synthesis of a phosphatidylinositol dimannoside (PIM2) analogue 4 that mimics the suppressive activity of natural PIMs and also synthetic PIM2 have been developed. This analogue, where the inositol core was replaced by glycerol, was tested for its ability to suppress cellular inflammation in a mouse model of allergic asthma and shown to be effective in suppressing airway eosinophilia. Suppression of all inflammatory cells monitored was observed, indicating a general blockade of cellular activity. These data indicate that the inositol core is not essential for this suppressive activity. (C) 2010 Elsevier Ltd. All rights reserved.
• Stereoselective Synthesis of α-Glycosyl Phosphites and Phosphoramidites via <i>O</i>-Selective Glycosylation of <i>H</i>-Phosphonate Derivatives
  作者：Fumiko Matsumura、Natsuhisa Oka、Takeshi Wada

  DOI：10.1021/ol802190x

  日期：2008.11.20

  A highly stereo- and chemoselective glycosylation of H-phosphonate derivatives with glycosyl iodides was discovered as a reverse reaction of the formation of a glycosyl iodide from a glycosyl phosphite and I- under mild acidic conditions. Further study on the unique reaction showed that the reaction provided various alpha-glycosyl phosphites; and phosphoramidites in a highly stereoselective manner with complete O-selectivity.
• [EN] SYNTHETIC MOLECULES HAVING IMMUNE ACTIVITY<br/>[FR] MOLECULES SYNTHETIQUES A IMMUNO-ACTIVITE
  申请人：MALAGHAN INST OF MEDICAL RES

  公开号：WO2005049631A1

  公开（公告）日：2005-06-02

  The present invention is directed to synthetic molecules having biological activity similar to PIM (acyl glycerol phosphatidylinositol manno-oligosaccharide) activity, for use in the treatment and prevention of inflammatory or immune cell mediated diseases or disorders.

  本发明涉及具有类似于PIM（酰基甘油磷脂肌醇寡糖）活性的合成分子，用于治疗和预防炎症性或免疫细胞介导的疾病或紊乱。
• Phosphatidylinositol mannosides: Synthesis and suppression of allergic airway disease
  作者：Gary D. Ainge、Jennifer Hudson、David S. Larsen、Gavin F. Painter、Gurmit Singh Gill、Jacquie L. Harper

  DOI：10.1016/j.bmc.2006.04.037

  日期：2006.8

  Phosphatidylinositol mannoside (PIM) extracts from mycobacteria have been shown previously to suppress allergic airway inflammation in mice. To help determine the structural requirements for activity, PIM1(2) (1), PIM1(6) (2) and PIM2 (3) were synthesized and tested for their ability to suppress cellular inflammation in a mouse model of allergic asthma. The synthetic PIMs were all effective in suppressing

  先前已证明，分枝杆菌的磷脂酰肌醇甘露糖苷（PIM）提取物可抑制小鼠的过敏性气道炎症。为了帮助确定活性的结构要求，合成了PIM1（2）（1），PIM1（6）（2）和PIM2（3），并测试了它们在变应性哮喘小鼠模型中抑制细胞炎症的能力。合成的PIM在哮喘模型中均能有效抑制气道嗜酸性粒细胞增多，其中PIM1（6）最有效。观察到所监测的所有炎性细胞的抑制，表明细胞炎的普遍阻断。非甘露糖基化磷脂酰肌醇（PI）没有抑制作用，表明至少一个α-d-甘露聚糖基对活性是必需的。