methyl (4-O-acetyl-3-acetamido-2-O-benzyl-3-deoxy-α-D-fucopyranosyl)-(1->3)-4-O-benzyl-α-L-rhamnopyranoside | 857254-32-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (4-O-acetyl-3-acetamido-2-O-benzyl-3-deoxy-α-D-fucopyranosyl)-(1->3)-4-O-benzyl-α-L-rhamnopyranoside
• CAS: 857254-32-1
• 化学式: C₃₁H₄₁NO₁₀
• 分子量: 587.667
• InChiKey: YVJFDEPKSOKWQW-ZVHQSAAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.48
• 重原子数：
  42.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  131.01
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  methyl (4-O-acetyl-3-acetamido-2-O-benzyl-3-deoxy-α-D-fucopyranosyl)-(1->3)-4-O-benzyl-α-L-rhamnopyranoside 、 (2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate 在 4 A molecular sieve 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以51%的产率得到
  参考文献：
  名称：

  First synthesis of an α-d-Fucp3NAc containing oligosaccharide: a study on d-Fucp3NAc glycosylation

  摘要：

  3-Acetainido-3.6-dideoxy-D-galactopyranose (D-Fucp3NAc) is an aminosugar almost exclusively found in phytopathogenic O-antigens. The glycosylation reaction involving D-Fucp3NAc donors was studied with several rhamnosyl acceptors, revealing, that the best yields and highest alpha-stereoselectivity were obtainable by coupling a N-phenyl trifluoroacetimidate glycosyl donor in a tertiary mixture (dioxane/DME/toluene 4:1:1) as solvent. For the first time a synthetic access to alpha-D-Fucp3NAc containing oligorhamnans, that are interesting molecules for studying the effects of O-antigen model oligosaccharides on the modulation of plant response to bacteria, was reported. An example is the pentasaccharide repeating unit of the major O-antigen component from Pseudomonas syringae pv. holci IMV 8300, which was synthesized as its methyl glycoside. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.04.013
• 作为产物：
  描述：

  4-O-acetyl-3-acetamido-2-O-benzyl-3-deoxy-D-fucopyranosyl N-phenyl-trifuoroacetimidate 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 palladium dichloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 methyl (4-O-acetyl-3-acetamido-2-O-benzyl-3-deoxy-α-D-fucopyranosyl)-(1->3)-4-O-benzyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  First synthesis of an α-d-Fucp3NAc containing oligosaccharide: a study on d-Fucp3NAc glycosylation

  摘要：

  3-Acetainido-3.6-dideoxy-D-galactopyranose (D-Fucp3NAc) is an aminosugar almost exclusively found in phytopathogenic O-antigens. The glycosylation reaction involving D-Fucp3NAc donors was studied with several rhamnosyl acceptors, revealing, that the best yields and highest alpha-stereoselectivity were obtainable by coupling a N-phenyl trifluoroacetimidate glycosyl donor in a tertiary mixture (dioxane/DME/toluene 4:1:1) as solvent. For the first time a synthetic access to alpha-D-Fucp3NAc containing oligorhamnans, that are interesting molecules for studying the effects of O-antigen model oligosaccharides on the modulation of plant response to bacteria, was reported. An example is the pentasaccharide repeating unit of the major O-antigen component from Pseudomonas syringae pv. holci IMV 8300, which was synthesized as its methyl glycoside. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.04.013