2-bromoethyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-β-D-galactopyranosyl-(1->4)-3,6-di-O-acetyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside | 903574-93-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-bromoethyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-β-D-galactopyranosyl-(1->4)-3,6-di-O-acetyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside
• CAS: 903574-93-6
• 化学式: C₃₂H₃₃BrCl₄N₄O₁₆
• 分子量: 951.347
• InChiKey: BHUUDYCWFOQFPE-CULFNUSISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.11
• 重原子数：
  57.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  254.56
• 氢给体数：
  0.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  2-bromoethyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-β-D-galactopyranosyl-(1->4)-3,6-di-O-acetyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside 在 palladium on activated charcoal 吡啶 、 盐酸 、 sodium azide 、 15-冠醚-5 、 氢气 、 sodium methylate 、 乙二胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0~60.0 ℃ 、101.33 kPa 条件下， 反应 38.84h， 生成 Naphthalene-2-carboxylic acid {(2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6R)-5-acetylamino-6-(2-amino-ethoxy)-4-hydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl}-amide
  参考文献：
  名称：

  Synthesis of a 3′-naphthamido-LacNAc fluorescein conjugate with high selectivity and affinity for galectin-3

  摘要：

  Described is the synthesis of a fluorescent LacNAc derivative appended with a 3-deoxy-3'-naphthamido functionality, 2-(fluorescein-5/6-amido)ethyl 3-deoxy-3-(2-naphthamido)-beta-D-galactopyranosyl-(1 -> 4)-2-acetamido-2-deoxy-beta-D-glucopyranoside, which confers high affinity (K-d 170 nM) and selectivity for galectin-3 via a stacking interaction with Arg144. Its use as a selective and sensitive galectin-3 probe is demonstrated with fluorescence polarization measurements. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.04.027
• 作为产物：
  描述：

  methyl 3-azido-3-deoxy-1-thio-β-D-galactoside 在 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 molecular sieve 、 三氟甲磺酸 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 生成 2-bromoethyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-β-D-galactopyranosyl-(1->4)-3,6-di-O-acetyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a 3′-naphthamido-LacNAc fluorescein conjugate with high selectivity and affinity for galectin-3

  摘要：

  Described is the synthesis of a fluorescent LacNAc derivative appended with a 3-deoxy-3'-naphthamido functionality, 2-(fluorescein-5/6-amido)ethyl 3-deoxy-3-(2-naphthamido)-beta-D-galactopyranosyl-(1 -> 4)-2-acetamido-2-deoxy-beta-D-glucopyranoside, which confers high affinity (K-d 170 nM) and selectivity for galectin-3 via a stacking interaction with Arg144. Its use as a selective and sensitive galectin-3 probe is demonstrated with fluorescence polarization measurements. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.04.027