4-O-acetyl-3-acetamido-2-O-benzyl-3-deoxy-D-fucopyranosyl N-phenyl-trifuoroacetimidate | 720694-52-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-acetyl-3-acetamido-2-O-benzyl-3-deoxy-D-fucopyranosyl N-phenyl-trifuoroacetimidate
• 英文别名: [(2R,3R,4S,5R)-4-acetamido-2-methyl-5-phenylmethoxy-6-[N-phenyl-C-(trifluoromethyl)carbonimidoyl]oxyoxan-3-yl] acetate
• CAS: 720694-52-0
• 化学式: C₂₅H₂₇F₃N₂O₆
• 分子量: 508.494
• InChiKey: WDZJHCZZUHYMDI-QXGRGYMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  95.4
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (3aR,4R,6S,7R,7aR)-6-Allyloxy-4-methyl-2-trichloromethyl-3a,6,7,7a-tetrahydro-4H-pyrano[4,3-d]oxazol-7-ol 在 盐酸 、 sodium hydride 、 palladium dichloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-O-acetyl-3-acetamido-2-O-benzyl-3-deoxy-D-fucopyranosyl N-phenyl-trifuoroacetimidate
  参考文献：
  名称：

  First preparative synthesis of a 3-acetamido-3,6-dideoxy-d-galactopyranose glycosyl donor via intramolecular cyclization of an epoxytrichloroacetimidate

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2004.04.065

文献信息

• First Synthesis of the β-<scp>d</scp>-Rhamnosylated Trisaccharide Repeating Unit of the <i>O</i>-Antigen from <i>Xanthomonas </i><i>c</i><i>ampestris </i>pv. <i>c</i><i>ampestris </i>8004
  作者：Emiliano Bedini、Antonella Carabellese、Gaspare Barone、Michelangelo Parrilli

  DOI：10.1021/jo051153d

  日期：2005.9.1

  The trisaccharide repeating unit of the O-antigen of the lipopolysaccharide from Xanthomonas campestris pv. campestris 8004, a pathogen of cruciferous crops, presents some structural features that renders it a challenging synthetic target: the presence of a β-d-rhamnosidic linkage, the steric crowd on a 1,2-cis-diglycosylated d-rhamnose, and finally the noncommercial availability of its monosaccharide

  来自野油菜黄单胞菌（Xanthomonas campestris pv）的脂多糖的O-抗原的三糖重复单元。十字花科作物的病原体campestris 8004具有一些结构特征，使其成为具有挑战性的合成靶标：β- d-鼠李糖苷键的存在，1,2-顺式-二糖基化d-鼠李糖上的位阻分子，最后单糖成分的非商业可用性。这种三糖作为甲基糖苷的合成已经通过采用一种策略来完成，该策略的关键步骤是用2- O-苄基磺酰基-N依次进行β- d-鼠李糖基化反应-苯基三氟乙酰亚氨酸酯供体，脱苄基磺酰化，并与d -Fuc p 3NAc硫代糖苷供体偶联。