p-methoxyphenyl 3,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside | 1225290-00-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 3,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• 英文别名: p-methoxyphenyl 3,6-di-O-acetyl-2-deoxy-2-phthalimdo-β-D-glucopyranoside
• CAS: 1225290-00-5
• 化学式: C₂₅H₂₅NO₁₀
• 分子量: 499.474
• InChiKey: XBOMPBIBZHYRPS-ANOZEODCSA-N

物化性质

• 沸点：
  653.9±55.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.32
• 重原子数：
  36.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  137.9
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 3,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 、 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-O-trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到p-methoxyphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and cytotoxic activity of the N-acetylglucosamine-bearing triterpenoid saponins

  摘要：

  Fourteen ursolic acid and oleanolic acid saponins with N-acetyl-beta-D-glucosamine, and (1 -> 4)-linked and (1 6)-linked N-acetyl-beta-D-glucosamine oligosaccharide residues were synthesized in a convergent manner. The structures of all compounds were confirmed by (1)H NMR and (13)C NMR spectroscopy and by mass spectrometry, and their cytotoxic activities were assayed in three cancer cell lines. Only oleanolic acid-3-yl beta-D-GluNAc showed significant cytotoxicity against HL-60 and BGC-823. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2010.01.002
• 作为产物：
  描述：

  p-methoxyphenyl 6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 perchloric acid on silica gel 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 生成 p-methoxyphenyl 3,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  An efficient and recyclable catalyst for the cleavage of tert-butyldiphenylsilyl ethers

  摘要：

  An efficient, chemoselective, and environment-friendly method for the deprotection of tert-butyldiphenylsilyl ethers mediated by triflic acid supported on silica gel is reported. A wide range of tert-butyldiphenylsilyl ethers derived from carbohydrate and saponin residues can be smoothly cleaved in the presence of various types of other protecting groups in good to excellent yields in acetonitrile. This heterogeneous reaction does not require aqueous workup, and the supported catalyst can be readily recycled. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.02.021