benzyl 3-O-allyl-4-O-benzoyl-α-L-rhamnopyranoside | 671790-37-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 3-O-allyl-4-O-benzoyl-α-L-rhamnopyranoside
• 英文别名: [(2S,3S,4S,5R,6R)-5-hydroxy-2-methyl-6-phenylmethoxy-4-prop-2-enoxyoxan-3-yl] benzoate
• CAS: 671790-37-7
• 化学式: C₂₃H₂₆O₆
• 分子量: 398.456
• InChiKey: COGREBSZKQMFLL-DYTUJVSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl 3-O-allyl-4-O-benzoyl-α-L-rhamnopyranoside 在 4-二甲氨基吡啶 、 N,N'-diisopropylaminopyridine 、 palladium dichloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 benzyl 4-O-benzoyl-2-O-levulinoyl-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
• 作为产物：
  描述：

  benzyl 4-O-benzoyl-α-L-rhamnopyranoside 、 3-溴丙烯 在 二正丁基氧化锡 、 四丁基溴化铵 作用下， 以 甲醇 、 苯 、 甲苯 为溶剂， 反应 3.0h， 以85%的产率得到benzyl 3-O-allyl-4-O-benzoyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of the pentasaccharide repeating unit of the major O-antigen component from Pseudomonas syringae pv. ribicola NVPPB 1010

  摘要：

  The synthesis of the repeating unit of the major O-antigen component from Pseudomonas syringae pv. ribicola NVPPB 1010 is reported. The strategy used was based on the successive coupling of a trisaccharide rhamnosyl trichloroacetimidate with a rhamnosyl acceptor with a free hydroxyl group on C-2. The pentasaccharide was then obtained by coupling with a N-Troc-tri-O-acetyl-glucosamine trichloroacetimidate. The synthesis allowed the oligomerisation of the repeating unit. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2003.10.002

文献信息

• First preparative synthesis of a 3-acetamido-3,6-dideoxy-d-galactopyranose glycosyl donor via intramolecular cyclization of an epoxytrichloroacetimidate
  作者：Emiliano Bedini、Alfonso Iadonisi、Antonella Carabellese、Michelangelo Parrilli

  DOI：10.1016/j.tetlet.2004.04.065

  日期：2004.5

  The preparative synthesis of a 3 -acetamido- 3,6-dideoxy -D-galactopyranose N-phenyl-trifluoroacetimidate donor has been accomplished using as key step a silica gel mediated cyclization of an epoxytrichloroacetimidate, while other more conventional routes to aminosugars failed. Test glycosylations with the N-phenyl-trifluoroacetimidate donor are also reported. (C) 2004 Elsevier Ltd. All rights reserved.
• First synthesis of an α-d-Fucp3NAc containing oligosaccharide: a study on d-Fucp3NAc glycosylation
  作者：Emiliano Bedini、Antonella Carabellese、Marialuisa Schiattarella、Michelangelo Parrilli

  DOI：10.1016/j.tet.2005.04.013

  日期：2005.6

  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.
• Synthesis of the pentasaccharide repeating unit of the major O-antigen component from Pseudomonas syringae pv. ribicola NVPPB 1010
  作者：Emiliano Bedini、Gaspare Barone、Carlo Unverzagt、Michelangelo Parrilli

  DOI：10.1016/j.carres.2003.10.002

  日期：2004.1

  The synthesis of the repeating unit of the major O-antigen component from Pseudomonas syringae pv. ribicola NVPPB 1010 is reported. The strategy used was based on the successive coupling of a trisaccharide rhamnosyl trichloroacetimidate with a rhamnosyl acceptor with a free hydroxyl group on C-2. The pentasaccharide was then obtained by coupling with a N-Troc-tri-O-acetyl-glucosamine trichloroacetimidate. The synthesis allowed the oligomerisation of the repeating unit. (C) 2003 Elsevier Ltd. All rights reserved.