octyl 3-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-2-amino-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside | 912364-42-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: octyl 3-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-2-amino-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5S,6R)-2-[[(2R,4aR,6R,7R,8R,8aS)-7-amino-6-octoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 912364-42-2
• 化学式: C₅₀H₆₃NO₁₁
• 分子量: 854.05
• InChiKey: GEDOXKHKBLPUIR-UPVWIGSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  62
• 可旋转键数：
  23
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  octyl 3-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-2-amino-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 在 吡啶 、 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 生成 N-[(2R,4aR,6R,7R,8R,8aS)-8-((2R,3R,4S,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-cyclohexylmethoxy-tetrahydro-pyran-2-yloxy)-6-octyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide
  参考文献：
  名称：

  Screening for Galectin-3 Inhibitors from Synthetic Lacto-N-biose Libraries Using Microscale Affinity Chromatography Coupled to Mass Spectrometry

  摘要：

  The synthesis and screening of two beta-D-Galp-(1-3)-beta-D-GlcpN ( lacto-N-biose) disaccharide libraries are reported. Solution-phase synthetic modifications at the HO-2' and NH positions were performed in an effort to enhance the affinity toward galectin-3, a galactose-binding protein involved in tumor metastasis, apoptosis, and inflammation. The libraries were screened for galectin-3 binding by microscale frontal affinity chromatography coupled to mass spectrometry ( FAC/MS) allowing for rapid ranking of the different inhibitors and the determination of the galectin-3 binding K-d's. Compounds bearing a hydrophobic substituent on the NH group showed the highest affinity for the lectin. The N-naphthoyl derivative ( K-d = 10.6 mu M) was the best inhibitor with a 7 times increased affinity as compared to the N-acetyl parent compound ( K-d = 73.3 mu M).

  DOI：

  10.1021/jo060485v
• 作为产物：
  描述：

  octyl 3-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-4,6-O-benzylidene-2-deoxy-2-[[(2,2,2-trichloroethoxy)carbonyl]amino]-β-D-glucopyranoside 在 溶剂黄146 、 锌 作用下， 反应 4.0h， 以75%的产率得到octyl 3-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-2-amino-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Screening for Galectin-3 Inhibitors from Synthetic Lacto-N-biose Libraries Using Microscale Affinity Chromatography Coupled to Mass Spectrometry

  摘要：

  The synthesis and screening of two beta-D-Galp-(1-3)-beta-D-GlcpN ( lacto-N-biose) disaccharide libraries are reported. Solution-phase synthetic modifications at the HO-2' and NH positions were performed in an effort to enhance the affinity toward galectin-3, a galactose-binding protein involved in tumor metastasis, apoptosis, and inflammation. The libraries were screened for galectin-3 binding by microscale frontal affinity chromatography coupled to mass spectrometry ( FAC/MS) allowing for rapid ranking of the different inhibitors and the determination of the galectin-3 binding K-d's. Compounds bearing a hydrophobic substituent on the NH group showed the highest affinity for the lectin. The N-naphthoyl derivative ( K-d = 10.6 mu M) was the best inhibitor with a 7 times increased affinity as compared to the N-acetyl parent compound ( K-d = 73.3 mu M).

  DOI：

  10.1021/jo060485v