(1R,3S,4S,6R,9S,10R)-10-hydroxy-3,4-dimethoxy-3,4-dimethyl-9-(2-naphthyl)oxy-2,5,8-trioxabicyclo[4.4.0]decane | 1315279-62-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,3S,4S,6R,9S,10R)-10-hydroxy-3,4-dimethoxy-3,4-dimethyl-9-(2-naphthyl)oxy-2,5,8-trioxabicyclo[4.4.0]decane
• CAS: 1315279-62-9
• 化学式: C₂₁H₂₆O₇
• 分子量: 390.433
• InChiKey: WKCKHKXXBGPUME-OFELHODLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  75.61
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (1R,3S,4S,6R,9S,10R)-10-hydroxy-3,4-dimethoxy-3,4-dimethyl-9-(2-naphthyl)oxy-2,5,8-trioxabicyclo[4.4.0]decane 在 咪唑 、 sodium hydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.25h， 生成 2-naphthyl 2-O-(methylthio)thiocarbonyl-β-D-threopyranoside
  参考文献：
  名称：

  Synthesis, conformation and biology of naphthoxylosides

  摘要：

  Proteoglycans (PG) are polyanionic proteins consisting of a core protein substituted with carbohydrate chains, that is, glycosaminoglycans (GAG). The biosynthesis of GAG can be manipulated by simple xylosides carrying hydrophobic aglycons, which can enter the cell and initiate the biosynthesis. While the importance of the aglycon is well investigated, there is far less information on the effect of modifications in the xylose residue.We have developed a new synthetic protocol, based on acetal protection and selective benzylation, for modification of the three hydroxyl groups in xylose. Thus we have synthesized twelve analogs of 2-naphthyl beta-D-xylopyranoside (XylNap), where each hydroxyl group has been epimerized or replaced by methoxy, fluoro, or hydrogen.To gain more information about the properties of xylose, conformational studies were made on some of the analogs. It was found that the (4)C(1) conformation is highly predominant, accompanied by a nonnegligible population of the (2)S(0) conformation. However, deoxygenation at C3 results in a large portion of the (1)C(4) conformation.The GAG priming ability and proliferation activity of the twelve analogs, were investigated using a matched pair of human breast fibroblasts and human breast carcinoma cells. None of the analogs initiated the biosynthesis of GAG, but an inhibitory effect on endogenous PG production was observed for analogs fluorinated or deoxygenated at C4. From our data it seems reasonable that all three hydroxyl groups in XylNap are essential for the priming of GAG chains and for selective toxicity for tumor cells. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.007
• 作为产物：
  描述：

  2,2,3,3-四甲氧基丁烷 、 naphth-2-yl β-D-xylopyranoside 在 三氟化硼乙醚 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以61%的产率得到(1R,3S,4S,6R,9S,10R)-10-hydroxy-3,4-dimethoxy-3,4-dimethyl-9-(2-naphthyl)oxy-2,5,8-trioxabicyclo[4.4.0]decane
  参考文献：
  名称：

  Synthesis, conformation and biology of naphthoxylosides

  摘要：

  Proteoglycans (PG) are polyanionic proteins consisting of a core protein substituted with carbohydrate chains, that is, glycosaminoglycans (GAG). The biosynthesis of GAG can be manipulated by simple xylosides carrying hydrophobic aglycons, which can enter the cell and initiate the biosynthesis. While the importance of the aglycon is well investigated, there is far less information on the effect of modifications in the xylose residue.We have developed a new synthetic protocol, based on acetal protection and selective benzylation, for modification of the three hydroxyl groups in xylose. Thus we have synthesized twelve analogs of 2-naphthyl beta-D-xylopyranoside (XylNap), where each hydroxyl group has been epimerized or replaced by methoxy, fluoro, or hydrogen.To gain more information about the properties of xylose, conformational studies were made on some of the analogs. It was found that the (4)C(1) conformation is highly predominant, accompanied by a nonnegligible population of the (2)S(0) conformation. However, deoxygenation at C3 results in a large portion of the (1)C(4) conformation.The GAG priming ability and proliferation activity of the twelve analogs, were investigated using a matched pair of human breast fibroblasts and human breast carcinoma cells. None of the analogs initiated the biosynthesis of GAG, but an inhibitory effect on endogenous PG production was observed for analogs fluorinated or deoxygenated at C4. From our data it seems reasonable that all three hydroxyl groups in XylNap are essential for the priming of GAG chains and for selective toxicity for tumor cells. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.007