((3aR,4S,6R,7R,7aS)-6-Azidomethyl-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl)-acetic acid methyl ester | 176257-43-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: ((3aR,4S,6R,7R,7aS)-6-Azidomethyl-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl)-acetic acid methyl ester
• 英文别名: methyl 2-[(3aR,4S,6R,7R,7aS)-6-(azidomethyl)-7-hydroxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]acetate
• CAS: 176257-43-5
• 化学式: C₁₂H₁₉N₃O₆
• 分子量: 301.299
• InChiKey: AUXBYNAWBCVXHT-MNGNJOOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  88.6
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ((3aR,4S,6R,7R,7aS)-6-Azidomethyl-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl)-acetic acid methyl ester 在 sodium hydroxide 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 作用下， 生成 (S)-2-[2-((3aR,4S,6R,7R,7aS)-6-Azidomethyl-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl)-acetylamino]-pentanedioic acid di-tert-butyl ester
  参考文献：
  名称：

  β-C-Mannosides as Selectin Inhibitors

  摘要：

  Potential E- and P-selectin inhibitors were synthesized to explore a hydrophobic area on the E-selectin surface and the PSGL-1 protein binding site on the P-selectin surface that was recently defined by crystallography. Three series of mannose-based compounds (libraries A, B, and C) were synthesized using solution phase parallel synthesis. Biological evaluation of these compounds was done using two ELISA-based assays and transferred NOE (trNOE) experiments. Some of the compounds showed better activity than sLe(x) in the P-selectin assay.

  DOI：

  10.1021/jm010390f
• 作为产物：
  描述：

  ((3R,4R,5R,6R)-3,4,5-Triacetoxy-6-azidomethyl-tetrahydro-pyran-2-yl)-acetic acid 在 lithium methanolate 、 4-甲基苯磺酸吡啶 、 碳酸氢钠 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.5h， 生成 ((3aR,4S,6R,7R,7aS)-6-Azidomethyl-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl)-acetic acid methyl ester
  参考文献：
  名称：

  糖胺酸：组合合成的新构件

  摘要：

  为了生产更适合用于组合有机合成的廉价、化学上多样化的碳水化合物结构单元，胺和羧酸官能团被加入到几种单糖中。一系列 12 种新的糖氨基酸是从市售的起始材料中制备的。传统的肽合成溶液偶联技术用于连接糖氨基酸，产生寡聚“糖苷”。最后，通过将糖氨基酸混合物偶联到刚性模板上产生糖苷库。

  DOI：

  10.1021/ja9525622