2-bromoethyl 6-O-acetyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside | 903574-91-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-bromoethyl 6-O-acetyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside
• CAS: 903574-91-4
• 化学式: C₁₈H₁₆BrCl₄NO₈
• 分子量: 596.043
• InChiKey: ADEGWCWQVKHDAS-HVVQHCOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  122.6
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-bromoethyl 6-O-acetyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside 在 palladium on activated charcoal 盐酸 、 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 molecular sieve 、 三氟甲磺酸 、 氢气 作用下， 以 吡啶 、 乙醇 、 二氯甲烷 为溶剂， -42.0~20.0 ℃ 、101.33 kPa 条件下， 反应 1.17h， 生成 Acetic acid (2R,3S,4R,5R,6R)-2-acetoxymethyl-6-(2-bromo-ethoxy)-3-((2S,3R,4S,5R,6R)-3,5-diacetoxy-6-acetoxymethyl-4-amino-tetrahydro-pyran-2-yloxy)-5-(4,5,6,7-tetrachloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester
  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：

  2-bromoethyl 2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside 、 乙酰氯 在 2,4,6-三甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以87%的产率得到2-bromoethyl 6-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