(3R,4S,5S,6S)-2-(allyloxy)-4,5-bis(benzyloxy)-6-methyltetrahydro-2H-pyran-3-ol | 1609449-62-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4S,5S,6S)-2-(allyloxy)-4,5-bis(benzyloxy)-6-methyltetrahydro-2H-pyran-3-ol
• CAS: 1609449-62-8
• 化学式: C₂₃H₂₈O₅
• 分子量: 384.472
• InChiKey: BWPCQWFAXGYARB-CFLMPHEOSA-N

物化性质

• 沸点：
  518.6±50.0 °C(predicted)
• 密度：
  1.16±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  28.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3R,4S,5S,6S)-2-(allyloxy)-4,5-bis(benzyloxy)-6-methyltetrahydro-2H-pyran-3-ol 在 吡啶 、 4-二甲氨基吡啶 、 硫酸 、 溶剂黄146 作用下， 反应 6.0h， 生成 acetyl 2-O-acetyl-3,4-di-O-benzyl-L-rhamnoopyranoside
  参考文献：
  名称：

  Total Synthesis of the Antitumor Natural Product Polycarcin V and Evaluation of Its DNA Binding Profile

  摘要：

  The convergent total synthesis of polycarcin V, a gilvocarcin-type natural product that shows significant cytotoxicity with selectivity for nonsmall-cell lung cancer, breast cancer, and melanoma cells, has been achieved in 13 steps from 7, 8, and 22; the sequence features a stereoselective alpha-C-glycosylation reaction for the union of protected carbohydrate 7' and naphthol 8. The association constant for the binding of polycarcin V to duplex DNA is similar to that previously reported for gilvocarcin V.

  DOI：

  10.1021/ol501095w
• 作为产物：
  描述：

  allyl L-rhamnopyranoside 在 咪唑 、 bismuth(III) chloride 、 水 、 sodium hydride 、 二正丁基氧化锡 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 44.42h， 生成 (3R,4S,5S,6S)-2-(allyloxy)-4,5-bis(benzyloxy)-6-methyltetrahydro-2H-pyran-3-ol
  参考文献：
  名称：

  Total Synthesis of the Antitumor Natural Product Polycarcin V and Evaluation of Its DNA Binding Profile

  摘要：

  The convergent total synthesis of polycarcin V, a gilvocarcin-type natural product that shows significant cytotoxicity with selectivity for nonsmall-cell lung cancer, breast cancer, and melanoma cells, has been achieved in 13 steps from 7, 8, and 22; the sequence features a stereoselective alpha-C-glycosylation reaction for the union of protected carbohydrate 7' and naphthol 8. The association constant for the binding of polycarcin V to duplex DNA is similar to that previously reported for gilvocarcin V.

  DOI：

  10.1021/ol501095w