octyl 2-acetamido-3-O-(3,4,6-tri-O-benzyl-2-O-methoxycarbonylmethyl-β-D-galactopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside | 912364-45-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: octyl 2-acetamido-3-O-(3,4,6-tri-O-benzyl-2-O-methoxycarbonylmethyl-β-D-galactopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
• 英文别名: methyl 2-[(2R,3R,4S,5S,6R)-2-[[(2R,4aR,6R,7R,8R,8aS)-7-acetamido-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]oxyacetate
• CAS: 912364-45-5
• 化学式: C₅₃H₆₇NO₁₃
• 分子量: 926.114
• InChiKey: BTUFRSXBYOKAKH-APVUBYPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  67
• 可旋转键数：
  26
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  148
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  octyl 2-acetamido-3-O-(3,4,6-tri-O-benzyl-2-O-methoxycarbonylmethyl-β-D-galactopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 1.0h， 以91%的产率得到[(2R,3R,4S,5R,6R)-2-((2R,3R,4R,5S,6R)-3-Acetylamino-5-hydroxy-6-hydroxymethyl-2-octyloxy-tetrahydro-pyran-4-yloxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yloxy]-acetic acid
  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：

  1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose 在 吡啶 、 N-碘代丁二酰亚胺 、 camphor-10-sulfonic acid 、 氢溴酸 、 sodium methylate 、 silver trifluoromethanesulfonate 、 氰化汞 、 sodium hydride 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 21.5h， 生成 octyl 2-acetamido-3-O-(3,4,6-tri-O-benzyl-2-O-methoxycarbonylmethyl-β-D-galactopyranosyl)-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

文献信息

• Screening for Galectin-3 Inhibitors from Synthetic Lacto-<i>N</i>-biose Libraries Using Microscale Affinity Chromatography Coupled to Mass Spectrometry
  作者：Sébastien Fort、Hyo-Sun Kim、Ole Hindsgaul

  DOI：10.1021/jo060485v

  日期：2006.9.1

  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).