(3R,5S)-5-(2-phenylethyl)oxolane-2,3-diol | 1262043-30-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3R,5S)-5-(2-phenylethyl)oxolane-2,3-diol
• CAS: 1262043-30-0
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: VTUAFQDZERUVSY-WIKAKEFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,5S)-5-(2-phenylethyl)oxolane-2,3-diol 在 水 、 溴 、 barium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以94%的产率得到3,5,6-Trideoxy-6-(4-bromophenyl)-D-gulono-1,4-lactone
  参考文献：
  名称：

  Design and synthesis of harzialactone analogues: Promising anticancer agents

  摘要：

  New homologues of harzialactone were synthesized using D-glucose as chiral template. Wittig reaction to introduce aromatic moiety in 10 and chemoselective anomeric oxidation of 13 were used as key reactions in our synthesis. Anticancer activity of these target molecules was assessed against five cancer cell lines, P388D1, HL60, COLO-205, Zr-75-1 and HeLa. Both compound 5 and 6, showed significant activity against colon cancer (COLO-205) and cervical cancer (HeLa) and moderate with others. To the best of our knowledge, this is the first report of harzialactone analogues as potent inhibitors of human colon and cervical cancer. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.100
• 作为产物：
  描述：

  1,2-O-isopropylidene-3,5,6-trideoxy-6-phenyl-α-D-gulo-1,4-furanose 在 硫酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 (3R,5S)-5-(2-phenylethyl)oxolane-2,3-diol
  参考文献：
  名称：

  Design and synthesis of harzialactone analogues: Promising anticancer agents

  摘要：

  New homologues of harzialactone were synthesized using D-glucose as chiral template. Wittig reaction to introduce aromatic moiety in 10 and chemoselective anomeric oxidation of 13 were used as key reactions in our synthesis. Anticancer activity of these target molecules was assessed against five cancer cell lines, P388D1, HL60, COLO-205, Zr-75-1 and HeLa. Both compound 5 and 6, showed significant activity against colon cancer (COLO-205) and cervical cancer (HeLa) and moderate with others. To the best of our knowledge, this is the first report of harzialactone analogues as potent inhibitors of human colon and cervical cancer. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.100