naphthalene-2,3-diyl bis(2,3,4-tri-O-acetyl-β-D-xylopyranoside)

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: naphthalene-2,3-diyl bis(2,3,4-tri-O-acetyl-β-D-xylopyranoside)
• 英文别名: [(3R,4S,5R,6S)-4,5-diacetyloxy-6-[3-[(2S,3R,4S,5R)-3,4,5-triacetyloxyoxan-2-yl]oxynaphthalen-2-yl]oxyoxan-3-yl] acetate
• 化学式: C₃₂H₃₆O₁₆
• 分子量: 676.628
• InChiKey: ANEMBFCEXHLAFL-SBHPHKOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  48
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  195
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  naphthalene-2,3-diyl bis(2,3,4-tri-O-acetyl-β-D-xylopyranoside) 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以86%的产率得到naphthalene-2,3-diyl bis(β-D-xylopyranoside)
  参考文献：
  名称：

  Synthesis and biology of bis-xylosylated dihydroxynaphthalenes

  摘要：

  The 10 analogous bis-xylosylated dihydroxynaphthalenes have been synthesized and their chemical and biological properties investigated. The yield of the xylosylation reactions can be correlated to the electrostatic potential, and thus to the nucleophilicity, for the oxygen atoms of the dihydroxynaphthalenes. The bis-xylosylated compounds were more stable compared to the mono-xylosylated ones. They initiate priming of glycosaminoglycan chains to less extent but the priming proceeds in two directions. Contrary to the mono-xylosylated analogs, the tested compounds did not show any antiproliferative properties. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.02.020
• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-D-xylopyranosyl trichloroacetimidate 、 2,3-二羟基萘 在 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以58%的产率得到naphthalene-2,3-diyl bis(2,3,4-tri-O-acetyl-β-D-xylopyranoside)
  参考文献：
  名称：

  Synthesis and biology of bis-xylosylated dihydroxynaphthalenes

  摘要：

  The 10 analogous bis-xylosylated dihydroxynaphthalenes have been synthesized and their chemical and biological properties investigated. The yield of the xylosylation reactions can be correlated to the electrostatic potential, and thus to the nucleophilicity, for the oxygen atoms of the dihydroxynaphthalenes. The bis-xylosylated compounds were more stable compared to the mono-xylosylated ones. They initiate priming of glycosaminoglycan chains to less extent but the priming proceeds in two directions. Contrary to the mono-xylosylated analogs, the tested compounds did not show any antiproliferative properties. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.02.020

文献信息

• Synthesis and biology of bis-xylosylated dihydroxynaphthalenes
  作者：Richard Johnsson、Katrin Mani、Ulf Ellervik

  DOI：10.1016/j.bmc.2007.02.020

  日期：2007.4

  The 10 analogous bis-xylosylated dihydroxynaphthalenes have been synthesized and their chemical and biological properties investigated. The yield of the xylosylation reactions can be correlated to the electrostatic potential, and thus to the nucleophilicity, for the oxygen atoms of the dihydroxynaphthalenes. The bis-xylosylated compounds were more stable compared to the mono-xylosylated ones. They initiate priming of glycosaminoglycan chains to less extent but the priming proceeds in two directions. Contrary to the mono-xylosylated analogs, the tested compounds did not show any antiproliferative properties. (c) 2007 Elsevier Ltd. All rights reserved.