Phenyl 2,3,4-tri-O-benzyl-6-O-(3,4,6-tri-O-benzyl-2-O-pivaloyl-α-D-mannopyranosyl)-1-thio-α-D-mannopyranoside | 310870-42-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Phenyl 2,3,4-tri-O-benzyl-6-O-(3,4,6-tri-O-benzyl-2-O-pivaloyl-α-D-mannopyranosyl)-1-thio-α-D-mannopyranoside
• CAS: 310870-42-9
• 化学式: C₆₅H₇₀O₁₁S
• 分子量: 1059.33
• InChiKey: CARWJTMIECLLEK-XBLTXSTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.35
• 重原子数：
  77.0
• 可旋转键数：
  25.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  109.37
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  Phenyl 2,3,4-tri-O-benzyl-6-O-(3,4,6-tri-O-benzyl-2-O-pivaloyl-α-D-mannopyranosyl)-1-thio-α-D-mannopyranoside 在 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以97%的产率得到Phenyl 2,3,4-tri-O-benzyl-6-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Inositolphosphoglycan Mediators Structurally Related to Glycosyl Phosphatidylinositol Anchors: Synthesis, Structure and Biological Activity

  摘要：

  The preparation of the pseudopentasaccharide 1a, an inositolphosphoglycan (IPG) that contains the conserved linear structure of glycosyl phosphatidylinositol anchors (GPI anchors), was carried out by using a highly convergent 2+3-block synthesis approach which involves imidate and sulfoxide glycosylation reactions. The preferred solution conformation of this structure was determined by using NMR spectroscopy and molecular dynamics simulations prior to carrying out quantitative structure-activity relationship studies in connection with the insulin signalling process. The ability of 1a to stimulate lipogenesis in rat adipocites as well as to inhibit cAMP dependent protein kinase and to activate pyruvate dehydrogenase phosphatase was investigated. Compound 1a did not show any significant activity, which may be taken as a strong indication that the GPI anchors are not the precursors of the IPG mediators.

  DOI：

  10.1002/1521-3765(20001002)6:19<3608::aid-chem3608>3.0.co;2-q
• 作为产物：
  描述：

  tert-Butyl-diphenyl-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-silane 在 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸酐 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 7.0h， 生成 Phenyl 2,3,4-tri-O-benzyl-6-O-(3,4,6-tri-O-benzyl-2-O-pivaloyl-α-D-mannopyranosyl)-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Inositolphosphoglycan Mediators Structurally Related to Glycosyl Phosphatidylinositol Anchors: Synthesis, Structure and Biological Activity

  摘要：

  The preparation of the pseudopentasaccharide 1a, an inositolphosphoglycan (IPG) that contains the conserved linear structure of glycosyl phosphatidylinositol anchors (GPI anchors), was carried out by using a highly convergent 2+3-block synthesis approach which involves imidate and sulfoxide glycosylation reactions. The preferred solution conformation of this structure was determined by using NMR spectroscopy and molecular dynamics simulations prior to carrying out quantitative structure-activity relationship studies in connection with the insulin signalling process. The ability of 1a to stimulate lipogenesis in rat adipocites as well as to inhibit cAMP dependent protein kinase and to activate pyruvate dehydrogenase phosphatase was investigated. Compound 1a did not show any significant activity, which may be taken as a strong indication that the GPI anchors are not the precursors of the IPG mediators.

  DOI：

  10.1002/1521-3765(20001002)6:19<3608::aid-chem3608>3.0.co;2-q