Acetic acid (2R,3S,4R,5R)-5-azido-4-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yl ester | 310870-32-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3S,4R,5R)-5-azido-4-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yl ester
• CAS: 310870-32-7
• 化学式: C₂₈H₂₉N₃O₅S
• 分子量: 519.621
• InChiKey: MGDAOWMEBHNORQ-OYDXEKDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.92
• 重原子数：
  37.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  102.75
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,4R,5R)-5-azido-4-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yl ester 在 N-溴代丁二酰亚胺(NBS) 、 水 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 trichloroacetoimidoyl 4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-α/β-D-glucopyranoside
  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：

  2-azido-4,6-O-benzylidene-2-deoxy-1-thio-D-glucopyranoside 在 盐酸 、 4-二甲氨基吡啶 、 sodium hydride 、 sodium cyanoborohydride 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 Acetic acid (2R,3S,4R,5R)-5-azido-4-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yl ester
  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