((3aR,4S,5aR,9aR,9bR)-2,2,8,8-Tetramethyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxin-4-yl)-acetic acid methyl ester | 418771-10-5

• 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,5aR,9aR,9bR)-2,2,8,8-Tetramethyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxin-4-yl)-acetic acid methyl ester
• 英文别名: methyl 2-[(1R,2R,6R,7S,9R)-4,4,12,12-tetramethyl-3,5,8,11,13-pentaoxatricyclo[7.4.0.02,6]tridecan-7-yl]acetate
• CAS: 418771-10-5
• 化学式: C₁₅H₂₄O₇
• 分子量: 316.351
• InChiKey: MWZPRTKGSCGUTF-IINAIABHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ((3aR,4S,5aR,9aR,9bR)-2,2,8,8-Tetramethyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxin-4-yl)-acetic acid methyl ester 在 吡啶 、 水 、 溶剂黄146 作用下， 生成 [(3aR,4S,6R,7R,7aS)-7-Hydroxy-2,2-dimethyl-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-acetic acid methyl 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 氢气 作用下， 生成 ((3aR,4S,5aR,9aR,9bR)-2,2,8,8-Tetramethyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxin-4-yl)-acetic acid methyl 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.