7-(1-hydroxynaphthyl)-β-D-xylopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-(1-hydroxynaphthyl)-β-D-xylopyranoside
• 英文别名: (2S,3R,4S,5R)-2-(8-hydroxynaphthalen-2-yl)oxyoxane-3,4,5-triol
• 化学式: C₁₅H₁₆O₆
• 分子量: 292.288
• InChiKey: ZGKSFDQSARXOKJ-BARDWOONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 7-(1-hydroxynaphthyl)-β-D-xylopyranoside 在 吡啶 作用下， 以100%的产率得到7-(1-O-acetylnaphthyl)-2,3,4-tri-O-acetyl-β-D-xylopyranoside
  参考文献：
  名称：

  Antiproliferative effects of peracetylated naphthoxylosides

  摘要：

  The antiproliferative activity, and the capability of priming of glycosaminoglycan chains, of two series of peracetylated mono- and bis-xylosylated dihydroxynaphthalenes have been investigated for normal HFL-1 cells, as well as transformed T24 cells, and compared to the unprotected analogs. Our data show increased antiproliferative activity upon peracetylation, but a loss of selectivity towards T24 cells. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.01.065
• 作为产物：
  描述：

  1,7-二羟基萘 、 tetra-O-acetyl-β-D-xylopyranose 在 吡啶 、 4-二甲氨基吡啶 、 polystyrene resin-C₆H₄-pCH₂NHC(O)CH₂CH₂C(O)Cl 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 1.75h， 以14%的产率得到1-(7-hydroxynaphthyl)-β-D-xylopyranoside
  参考文献：
  名称：

  Synthesis of naphthoxylosides on solid support

  摘要：

  In order to investigate the selective antiproliferative effects shown by 2-(6-hydroxynaphthyl)-beta-D-xylopyranoside the 14 possible beta-D-xylopyranosidic compounds were synthesized on solid support. An aminomethylated polystyrene resin was converted into an acid chloride resin and then esterified using dihydroxynaphthalene. The free hydroxy group was then xylosylated Under BF3.OEt2 mediated conditions. The xyloside was deprotected and simultaneously cleaved off the resin Using NaOMe/MeOH. Final purification using reverse phase HPLC gave the pure xylosides in 6-42% yield with Virtually no formation of alpha-xylosides. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01467-3

文献信息

• Synthesis of naphthoxylosides on solid support
  作者：Mårten Jacobsson、Ulf Ellervik

  DOI：10.1016/s0040-4039(02)01467-3

  日期：2002.9

  In order to investigate the selective antiproliferative effects shown by 2-(6-hydroxynaphthyl)-beta-D-xylopyranoside the 14 possible beta-D-xylopyranosidic compounds were synthesized on solid support. An aminomethylated polystyrene resin was converted into an acid chloride resin and then esterified using dihydroxynaphthalene. The free hydroxy group was then xylosylated Under BF3.OEt2 mediated conditions. The xyloside was deprotected and simultaneously cleaved off the resin Using NaOMe/MeOH. Final purification using reverse phase HPLC gave the pure xylosides in 6-42% yield with Virtually no formation of alpha-xylosides. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Antiproliferative effects of peracetylated naphthoxylosides
  作者：Ulrika Nilsson、Mårten Jacobsson、Richard Johnsson、Katrin Mani、Ulf Ellervik

  DOI：10.1016/j.bmcl.2009.01.065

  日期：2009.3

  The antiproliferative activity, and the capability of priming of glycosaminoglycan chains, of two series of peracetylated mono- and bis-xylosylated dihydroxynaphthalenes have been investigated for normal HFL-1 cells, as well as transformed T24 cells, and compared to the unprotected analogs. Our data show increased antiproliferative activity upon peracetylation, but a loss of selectivity towards T24 cells. (C) 2009 Elsevier Ltd. All rights reserved.