allyl 2-O-benzyl-3-deoxy-4,3-(2-trichloromethyl-1-oxa-3-azaprop-2-eno)-α-D-fucopyranoside | 720694-46-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: allyl 2-O-benzyl-3-deoxy-4,3-(2-trichloromethyl-1-oxa-3-azaprop-2-eno)-α-D-fucopyranoside
• 英文别名: (3aR,4R,6S,7R,7aS)-4-methyl-7-phenylmethoxy-6-prop-2-enoxy-2-(trichloromethyl)-4,6,7,7a-tetrahydro-3aH-pyrano[4,3-d][1,3]oxazole
• CAS: 720694-46-2
• 化学式: C₁₈H₂₀Cl₃NO₄
• 分子量: 420.72
• InChiKey: XHVHGQNBQGGSIM-CHUNWDLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  allyl 2-O-benzyl-3-deoxy-4,3-(2-trichloromethyl-1-oxa-3-azaprop-2-eno)-α-D-fucopyranoside 在 盐酸 、 sodium hydride 、 palladium dichloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 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
• 作为产物：
  描述：

  2,2,2-Trichloro-acetimidic acid (1R,2S,4R,5S,6R)-2-allyloxy-4-methyl-3,7-dioxa-bicyclo[4.1.0]hept-5-yl ester 在 silica gel 、 sodium hydride 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 allyl 2-O-benzyl-3-deoxy-4,3-(2-trichloromethyl-1-oxa-3-azaprop-2-eno)-α-D-fucopyranoside
  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 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.