3-iodophenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside | 871311-13-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-iodophenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
• 英文别名: 3-Iodophenyl 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranoside；[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(3-iodophenoxy)oxan-2-yl]methyl acetate
• CAS: 871311-13-6
• 化学式: C₂₀H₂₃IO₁₀
• 分子量: 550.301
• InChiKey: UQROLRGYPOCGNJ-SLHNCBLASA-N

物化性质

• 沸点：
  550.6±50.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-iodophenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 在 四丁基溴化铵 、 palladium diacetate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以94%的产率得到3,3'-bis-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)biphenyl
  参考文献：
  名称：

  Palladium-Catalyzed Ullmann-Type Reductive Homocoupling of Iodoaryl Glycosides

  摘要：

  A catalytic synthesis of novel biaryl-linked divalent glycosides was achieved using an electroreductive palladium-catalyzed iodoaryl-iodoaryl coupling reaction. This new method was optimized for the synthesis of divalent biaryl-linked mannopyranosides that was subsequently generalized toward several carbohydrate substrates with yields up to 96%.

  DOI：

  10.1021/jo2025652
• 作为产物：
  描述：

  Α-D-五乙酸甘露糖酯 、 3-碘苯酚 在 三氟化硼乙醚 作用下， 以 甲苯 为溶剂， 反应 90.0h， 以56%的产率得到3-iodophenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
  参考文献：
  名称：

  [EN] MANNOSE PHOSPHATE DERIVATIVES AS ANTAGONISTS OF BACTERIAL ADHESION
  [FR] DÉRIVÉS DE MANNOSE PHOSPHATE EN TANT QU'ANTAGONISTES DE L'ADHÉSION BACTÉRIENNE

  摘要：

  公式(I)（I）化合物，其中n为0、1或2，R1为芳基、杂芳基或杂环基，R2和R3独立地为氢或如说明书中所描述的取代基，且RA、RB、RC和RD中的一个为P02(OH)2，其余为氢；是口服可用的药物，用于预防和治疗细菌感染，特别是由大肠杆菌引起的尿路感染。

  公开号：

  WO2012164074A1

文献信息

• MANNOSE DERIVATIVES AS ANTAGONISTS OF BACTERIAL ADHESION
  申请人：Ernst Beat

  公开号：US20120270824A1

  公开（公告）日：2012-10-25

  Compounds of the formula (I) wherein n is 0, 1 or 2, R 1 is aryl, heteroaryl or heterocyclyl, and R 2 and R 3 are hydrogen or a substituent as described in the specification, are useful for the prevention and treatment of bacterial infections, in particular of urinary infections caused by E. coli .

  式(I)的化合物，其中n为0、1或2，R1为芳基、杂芳基或杂环基，R2和R3为氢或规范中所述的取代基，对于预防和治疗细菌感染，特别是由大肠杆菌引起的尿路感染是有用的。
• Mannose derivatives as antagonists of bacterial adhesion
  申请人：University of Basel

  公开号：EP2604619A2

  公开（公告）日：2013-06-19

  Compounds of the formula (I) wherein n is 0, 1 or 2, R1 is aryl, heteroaryl or heterocyclyl, and R2 and R3 are hydrogen or a substituent as described in the specification, are useful for the prevention and treatment of bacterial infections, in particular of urinary infections caused by E. coli.

  式 (I) 的化合物 其中 n 为 0、1 或 2，R1 为芳基、杂芳基或杂环基，R2 和 R3 为氢或说明书中所述的取代基，可用于预防和治疗细菌感染，特别是由大肠杆菌引起的泌尿系统感染。
• PHENYL-ALPHA-D-MANNOSIDES FOR USE IN THE TREATMENT OF BACTERIAL INFECTIONS CAUSED BY ESCHERICHIA COLI
  申请人：University of Basel

  公开号：EP2960247A1

  公开（公告）日：2015-12-30

  Compounds of the formula (I) wherein n is 0, 1 or 2, R2 and R3 are hydrogen or a substituent as described in the specification, are useful for the prevention and treatment of bacterial infections, in particular of urinary infections caused by E. coli, wherein R1 is one of groups (B), (C), (D), (E) below:

  式（I）化合物，其中 n 为 0、1 或 2，R2 和 R3 为氢或说明书中所述的取代基，可用于预防和治疗细菌感染，特别是由大肠杆菌引起的泌尿系统感染、 其中 R1 为以下 (B)、(C)、(D)、(E) 组之一：
• [EN] MANNOSE DERIVATIVES AS ANTAGONISTS OF BACTERIAL ADHESION<br/>[FR] DÉRIVÉS DE MANNOSE UTILISÉS EN TANT QU'ANTAGONISTES DE L'ADHÉSION BACTÉRIENNE
  申请人：UNIV BASEL

  公开号：WO2011073112A3

  公开（公告）日：2011-09-09
• Synthesis of a small library of bivalent α-d-mannopyranosides for lectin cross-linking
  作者：Milan Bergeron-Brlek、Tze Chieh Shiao、M. Corazon Trono、René Roy

  DOI：10.1016/j.carres.2011.03.041

  日期：2011.9

  A small library of bivalent alpha-D-mannopyranosides having rigid linkers was constructed in order to evaluate the effects of inter-saccharide distances upon multivalent binding interactions with plant and bacterial lectins. To this end, iodoaryl and propargyl alpha-D-mannopyranosides were synthesized and the former treated with TMS-acetylene under palladium chemistry to provide their corresponding ethynylaryl derivatives. A library of 15 dimeric members was then obtained using Lewis acid catalyzed glycosidation, aryl-aryl homocoupling, transition metal catalyzed Sonogashira cross-coupling reactions, and oxidative Glaser homocoupling. (C) 2011 Elsevier Ltd. All rights reserved.