3-[2-(2-{[3-((2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propylcarbamoyl]-methoxy}-acetylamino)-ethoxy]-benzoic acid methyl ester | 848814-39-1

• 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-[2-(2-{[3-((2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propylcarbamoyl]-methoxy}-acetylamino)-ethoxy]-benzoic acid methyl ester
• CAS: 848814-39-1
• 化学式: C₃₁H₄₂N₂O₁₆
• 分子量: 698.678
• InChiKey: PIESWFJOWLETKZ-AWTCAUSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.41
• 重原子数：
  49.0
• 可旋转键数：
  19.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  226.62
• 氢给体数：
  2.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  3-[2-(2-{[3-((2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propylcarbamoyl]-methoxy}-acetylamino)-ethoxy]-benzoic acid methyl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以55%的产率得到methyl 3-[2-[[2-[2-oxo-2-[3-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropylamino]ethoxy]acetyl]amino]ethoxy]benzoate
  参考文献：
  名称：

  Novel multivalent mannose compounds and their inhibition of the adhesion of type 1 fimbriated uropathogenic E. coli

  摘要：

  A series of multivalent mannose containing compounds were prepared varying in size from small divalent, to 16-valent glycodenrimers and 21-valent glycopolymers. The molecules were approached via a common mannose building block. As scaffolds dendrimers and dendrons based on the 3,5-di-(2-aminoethoxy)-benzoic acid branching unit were used along with commercially available PAMAM dendrimers. To include larger structures, linear glycopolymers with varying amounts of mannose were prepared via radical polymerization. The compounds were tested for their biological activity using a newly developed ELISA based inhibition assay, for their ability to inhibit the binding of recombinant type I fimbriated E. coli to a monolayer of T24 cell line derived from human urinary bladder epithelium. All compounds showed enhanced affinity as compared to mannose with IC50's down to the low micromolar range. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.014
• 作为产物：
  描述：

  3-azidopropyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 在 palladium on activated charcoal 吡啶 、 氢气 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 3.0h， 生成 3-[2-(2-{[3-((2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propylcarbamoyl]-methoxy}-acetylamino)-ethoxy]-benzoic acid methyl ester
  参考文献：
  名称：

  Novel multivalent mannose compounds and their inhibition of the adhesion of type 1 fimbriated uropathogenic E. coli

  摘要：

  A series of multivalent mannose containing compounds were prepared varying in size from small divalent, to 16-valent glycodenrimers and 21-valent glycopolymers. The molecules were approached via a common mannose building block. As scaffolds dendrimers and dendrons based on the 3,5-di-(2-aminoethoxy)-benzoic acid branching unit were used along with commercially available PAMAM dendrimers. To include larger structures, linear glycopolymers with varying amounts of mannose were prepared via radical polymerization. The compounds were tested for their biological activity using a newly developed ELISA based inhibition assay, for their ability to inhibit the binding of recombinant type I fimbriated E. coli to a monolayer of T24 cell line derived from human urinary bladder epithelium. All compounds showed enhanced affinity as compared to mannose with IC50's down to the low micromolar range. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.014