(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 | 502423-61-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (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
• 英文别名: Bz(-2)[ClAc(-3)][Bz(-4)]Rha(a1-3)[Bz(-2)][Bz(-4)]Rha(a1-2)[Bz(-3)][Bz(-4)]Rha(a)-O-C(NH)CCl3；[(2S,3S,4R,5R,6S)-4-benzoyloxy-5-[(2S,3R,4R,5S,6S)-3,5-dibenzoyloxy-4-[(2S,3R,4R,5S,6S)-3,5-dibenzoyloxy-4-(2-chloroacetyl)oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-2-methyl-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] benzoate
• CAS: 502423-61-2
• 化学式: C₆₄H₅₇Cl₄NO₂₀
• 分子量: 1301.96
• InChiKey: ZWBDGACDKUSBCN-ZGKTYWCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.8
• 重原子数：
  89
• 可旋转键数：
  27
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  263
• 氢给体数：
  1
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  benzyl 3-O-allyl-4-O-benzoyl-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 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以79%的产率得到benzyl (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)-(1->2)-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
• 作为产物：
  描述：

  benzyl (2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzoyl-α-L-rhamnopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 三氯化铁 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 2.33h， 生成 (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
  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 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.
• Synthetic oligorhamnans related to the most common O-chain backbone from phytopathogenic bacteria
  作者：Emiliano Bedini、Antonella Carabellese、Daniela Comegna、Cristina De Castro、Michelangelo Parrilli

  DOI：10.1016/j.tet.2006.06.084

  日期：2006.9

  The synthesis of the tetrasaccharide rhamnanic motif alpha-L-Rha-(1 -> 3)-alpha-L-Rha-(1 -> 2)-alpha-L-Rha-(1 -> 2)-alpha-L-Rha and its dimerization to octasaccharide have been developed. Three different pathways toward the dimerization have been investigated; the best one was based on a [4+2]+2 stepwise condensation of a rhamnose tetrasaccharide with two rhamnosyl N-phenyl ttifluoroacetimidates as glycosyl donors and on an orthogonal set of protecting groups consisting of benzoyl, levulinoyl, and allyl groups. (c) 2006 Elsevier Ltd. All rights reserved.
• Structure-Dependent Modulation of a Pathogen Response in Plants by Synthetic O-Antigen Polysaccharides
  作者：Emiliano Bedini、Cristina De Castro、Gitte Erbs、Lorenzo Mangoni、J. Maxwell Dow、Mari-Anne Newman、Michelangelo Parrilli、Carlo Unverzagt

  DOI：10.1021/ja0452166

  日期：2005.3.1

  Many phytopathogenic bacteria display lipopolysaccharides (LIPS) with the O-chain repeating unit [alpha-L-Rha-(1-->3)-alpha-L-Rha-(1-->3)-alpha-L-Rha-(1-->2)](n). This trisaccharide unit was synthesized and oligomerized to obtain hexa- and nonasaccharides. The deprotected rhamnans were effective in suppressing the hypersensitive response (HR) and in inducing PR-1 gene expression in Arabidopsis thaliana. Conformational analysis of the oligorhamnans by NMR spectroscopy and molecular dynamics calculations revealed that a coiled structure develops with increasing chain length of the oligosaccharide. This is associated with increasing efficacy in HR suppression and PR-1 gene expression. We therefore infer that the coiled structure of phytopathogenic bacteria is a plant-recognizable pathogen-associated molecular pattern (PAMP).
• 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.