N-{2-Chloro-5-[(2R,3R,4R,5S,6R)-5-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-3,4-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl]-phenyl}-acetamide | 721942-70-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-{2-Chloro-5-[(2R,3R,4R,5S,6R)-5-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-3,4-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl]-phenyl}-acetamide
• CAS: 721942-70-7
• 化学式: C₂₃H₃₂ClNO₁₂
• 分子量: 549.96
• InChiKey: DPJJDWCMPAAOCF-VOJVVDSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.15
• 重原子数：
  37.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  185.63
• 氢给体数：
  6.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  苯甲酰氯 、 N-{2-Chloro-5-[(2R,3R,4R,5S,6R)-5-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-3,4-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl]-phenyl}-acetamide 在 2,3,5-三甲基吡啶 作用下， 以 四氢呋喃 为溶剂， 以54%的产率得到(R)-N-[5-[[[6-O-benzoyl-4-O-(4,6-O-ethylidene-α-D-glucopyranosyl)-β-D-glucopyranosyl]oxy]methyl]-2-chlorophenyl]acetamide
  参考文献：
  名称：

  Stability studies of C-4′,6′ acetal benzylmaltosides synthesized as inhibitors of smooth muscle cell proliferation

  摘要：

  In our investigations to synthesize inhibitors of smooth muscle cell (SMC) proliferation, compound 6a displayed sub-micromolar activity in in vitro antiproliferative assays and reduced intimal thickening using a rat balloon angioplasty model via iv administration. In order to identify analogs that could be administered orally, the chemical instability of the C-4',6' acetal of compound 6a was addressed. Several novel variants with increased acid stability and comparable in vitro activity were prepared. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.049
• 作为产物：
  描述：

  3-amino-4-chlorobenzyl hepta-O-acetyl-β-maltoside 在 甲醇 、 sodium methylate 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 N-{2-Chloro-5-[(2R,3R,4R,5S,6R)-5-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-3,4-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl]-phenyl}-acetamide
  参考文献：
  名称：

  Stability studies of C-4′,6′ acetal benzylmaltosides synthesized as inhibitors of smooth muscle cell proliferation

  摘要：

  In our investigations to synthesize inhibitors of smooth muscle cell (SMC) proliferation, compound 6a displayed sub-micromolar activity in in vitro antiproliferative assays and reduced intimal thickening using a rat balloon angioplasty model via iv administration. In order to identify analogs that could be administered orally, the chemical instability of the C-4',6' acetal of compound 6a was addressed. Several novel variants with increased acid stability and comparable in vitro activity were prepared. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.049