2,3,4,6-tetra-O-benzyl-D-mannopyranosyl dimethyl phosphite

• 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-D-mannopyranosyl dimethyl phosphite
• 英文别名: tetra-O-benzyl-D-mannopyranosyl phosphite；dimethyl [(3S,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl] phosphite
• 化学式: C₃₆H₄₁O₈P
• 分子量: 632.69
• InChiKey: NKFCEJUKCPDRQP-AMTMJGOGSA-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-D-mannopyranosyl dimethyl phosphite 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以39.8 mg的产率得到dimethyl 2,3,4,6-tetra-O-benzyl-D-mannopyranosyl boranophosphate
  参考文献：
  名称：

  Stereoselective Synthesis of α-Glycosyl Phosphites and Phosphoramidites via O-Selective Glycosylation of H-Phosphonate Derivatives

  摘要：

  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.

  DOI：

  10.1021/ol802190x
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-D-mannopyranose 、 N,N-二异丙基亚膦酸二甲酯酰胺 在 四氮唑 作用下， 以 二氯甲烷 为溶剂， 反应 0.83h， 生成 2,3,4,6-tetra-O-benzyl-D-mannopyranosyl dimethyl phosphite
  参考文献：
  名称：

  Glycosylation of alcohols using glycosyl boranophosphates as glycosyl donors

  摘要：

  A novel glycosylation that uses glycosyl boranophosphate triesters as glycosyl donors and trityl cation (Tr+) as an activator was developed. Two types of reactions were studied: (1) the boranophosphate triester was activated with TrNTf2 to react with an alcohol and (2) O-trityl ethers worked as both glycosyl acceptors and Tr+ sources. The latter gave better results and the desired O-glycosylation products were rapidly generated and isolated in moderate to good yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.04.032

文献信息

• [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。
• Synthetic Molecules Having Immune Activity
  申请人：Singh-Gill Gurmit

  公开号：US20080249037A1

  公开（公告）日：2008-10-09

  The present invention is directed to synthetic molecules having biological activity similar to PIM (acyl glycerol phosphatidylinositol manno-oligosacccharide) 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（酰基甘油磷酰肌醇低聚糖）活性的合成分子，用于治疗和预防由炎症或免疫细胞介导的疾病或障碍。
• 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.
• Regiospecific Synthesis of 2,6-Di-<i>O</i>- (α-<scp>d</scp>-mannopyranosyl)phosphatidyl-<scp>d</scp>-<i>myo</i>- inositol
  作者：Yutaka Watanabe、Takashi Yamamoto、Shoichiro Ozaki

  DOI：10.1021/jo951511k

  日期：1996.1.1
• US7989602B2
  申请人：——

  公开号：US7989602B2

  公开（公告）日：2011-08-02