(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 | 418771-14-9

• 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: (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
• 英文别名: ditert-butyl (2S)-2-[[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]acetyl]amino]pentanedioate
• CAS: 418771-14-9
• 化学式: C₂₄H₄₀N₄O₉
• 分子量: 528.603
• InChiKey: ASSHCQNXHWZRLC-XGAXWPDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  144
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (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 在 palladium on activated charcoal benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 作用下， 生成 (S)-2-[2-((3aR,4S,6R,7R,7aS)-7-Hydroxy-2,2-dimethyl-6-{[2-((S)-1-phenyl-ethylcarbamoyl)-benzoylamino]-methyl}-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：

  methyl 2-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)acetate 在 palladium on activated charcoal 吡啶 、 sodium hydroxide 、 sodium azide 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 水 、 氢气 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 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

文献信息

• β-C-Mannosides as Selectin Inhibitors
  作者：Neelu Kaila、Lihren Chen、Thomas、Desiree Tsao、Steve Tam、Patricia W. Bedard、Raymond T. Camphausen、Juan C. Alvarez、Giliyar Ullas

  DOI：10.1021/jm010390f

  日期：2002.4.1

  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.