(3R,4R,5S,6S)-2-(allyloxy)-4,5-bis(benzyloxy)-6-methyltetrahydro-2H-pyran-3-yl acetate | 1609449-89-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4R,5S,6S)-2-(allyloxy)-4,5-bis(benzyloxy)-6-methyltetrahydro-2H-pyran-3-yl acetate
• CAS: 1609449-89-9
• 化学式: C₂₅H₃₀O₆
• 分子量: 426.51
• InChiKey: DHDSUNVGCNSDEG-MCNQGZMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  31.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3R,4R,5S,6S)-2-(allyloxy)-4,5-bis(benzyloxy)-6-methyltetrahydro-2H-pyran-3-yl acetate 、 乙酸酐 在 硫酸 、 溶剂黄146 作用下， 反应 1.0h， 以4.1 g的产率得到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：

  (3aR,6S,7S,7aR)-2,2,6-trimethyl-4-prop-2-enoxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 bismuth(III) chloride 、 水 、 sodium hydride 、 二正丁基氧化锡 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 49.25h， 生成 (3R,4R,5S,6S)-2-(allyloxy)-4,5-bis(benzyloxy)-6-methyltetrahydro-2H-pyran-3-yl acetate
  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