(3S,4S,5R,6R)-2-Allyl-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ol | 140909-64-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4S,5R,6R)-2-Allyl-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ol
• 英文别名: (3S,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)-2-prop-2-enyloxan-2-ol
• CAS: 140909-64-4
• 化学式: C₃₇H₄₀O₆
• 分子量: 580.721
• InChiKey: PDXZGVJAFXZLPJ-XZWUEEEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.62
• 重原子数：
  43.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3S,4S,5R,6R)-2-Allyl-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ol 在 palladium on activated charcoal 盐酸 、 三乙基硅烷 、 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 三氟化硼乙醚 、 氢气 、 双氧水 作用下， 以 甲醇 、 乙醇 、 乙腈 为溶剂， 反应 27.0h， 生成 3-(α-D-mannopyranosyl)-1-propanol
  参考文献：
  名称：

  C-glycosyl compounds bind to receptors on the surface of Escherichia coli and can target proteins to the organism

  摘要：

  A series of C-mannopyranosyl derivatives have been synthesized and their inhibitory activity towards the receptor-mediated adhesion of E. coli to yeast cells has been tested. Total inhibition of yeast-cell agglutination by C-glycosyl derivatives 4 and 9 is achieved at a concentration approximately one order of magnitude lower than that of methyl alpha-D-mannopyranoside, indicating that the binding affinity to the receptor is related to the hydrophobicity of the carbon-linked side chain. A biotin-linked C-glycosyl derivative of mannose (compound 9) has been synthesized and used to target avidin and streptavidin to the bacterial cell surface. Of the C-glycosyl derivatives tested in our study, the conjugate of compound 9 with avidin had the highest avidity for the bacterial receptors, inhibiting agglutination at a concentration three orders of magnitude lower than methyl alpha-D-mannopyranoside. The use of such bifunctional compounds as the mannose-biotin conjugate 9 is a general strategy to target molecules to pathogenic organisms via their cell-surface carbohydrate receptors and to change the antigenicity of the bacterial cell surface.

  DOI：

  10.1016/0008-6215(92)80021-r
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-D-mannono-1,5-lactone 、 烯丙基溴化镁 以 四氢呋喃 为溶剂， 生成 (3S,4S,5R,6R)-2-Allyl-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ol
  参考文献：
  名称：

  C-glycosyl compounds bind to receptors on the surface of Escherichia coli and can target proteins to the organism

  摘要：

  A series of C-mannopyranosyl derivatives have been synthesized and their inhibitory activity towards the receptor-mediated adhesion of E. coli to yeast cells has been tested. Total inhibition of yeast-cell agglutination by C-glycosyl derivatives 4 and 9 is achieved at a concentration approximately one order of magnitude lower than that of methyl alpha-D-mannopyranoside, indicating that the binding affinity to the receptor is related to the hydrophobicity of the carbon-linked side chain. A biotin-linked C-glycosyl derivative of mannose (compound 9) has been synthesized and used to target avidin and streptavidin to the bacterial cell surface. Of the C-glycosyl derivatives tested in our study, the conjugate of compound 9 with avidin had the highest avidity for the bacterial receptors, inhibiting agglutination at a concentration three orders of magnitude lower than methyl alpha-D-mannopyranoside. The use of such bifunctional compounds as the mannose-biotin conjugate 9 is a general strategy to target molecules to pathogenic organisms via their cell-surface carbohydrate receptors and to change the antigenicity of the bacterial cell surface.

  DOI：

  10.1016/0008-6215(92)80021-r