(25R)-3β-[2,4-di-O-(2,3,4-tri-O-pivaloyl-α-L-rhamnopyranosyl)-3,6-di-O-pivaloyl-β-D-glucopyranosyloxy]-26-iodo-cholest-5-ene-16,22-dione | 902762-64-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (25R)-3β-[2,4-di-O-(2,3,4-tri-O-pivaloyl-α-L-rhamnopyranosyl)-3,6-di-O-pivaloyl-β-D-glucopyranosyloxy]-26-iodo-cholest-5-ene-16,22-dione
• 英文别名: [(2R,3R,4S,5R,6R)-4-(2,2-dimethylpropanoyloxy)-6-[[(3S,8S,9S,10R,13S,14S,17R)-17-[(2S,6R)-7-iodo-6-methyl-3-oxoheptan-2-yl]-10,13-dimethyl-16-oxo-1,2,3,4,7,8,9,11,12,14,15,17-dodecahydrocyclopenta[a]phenanthren-3-yl]oxy]-3,5-bis[[(2S,3R,4R,5S,6S)-3,4,5-tris(2,2-dimethylpropanoyloxy)-6-methyloxan-2-yl]oxy]oxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 902762-64-5
• 化学式: C₈₅H₁₃₅IO₂₄
• 分子量: 1667.9
• InChiKey: JKNBEMLEVKECDB-OHWQTGSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.2
• 重原子数：
  110
• 可旋转键数：
  37
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  300
• 氢给体数：
  0
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  (25R)-3β-[2,4-di-O-(2,3,4-tri-O-pivaloyl-α-L-rhamnopyranosyl)-3,6-di-O-pivaloyl-β-D-glucopyranosyloxy]-26-iodo-cholest-5-ene-16,22-dione 、 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl N-phenyltrifluoroacetimidate 在 silver nitrate 、 silver carbonate 、 三氟甲磺酸三甲基硅酯 、 5A molecular sieve 作用下， 以 水 、 丙酮 、 二氯甲烷 为溶剂， 反应 6.0h， 以54%的产率得到(25R)-3β-[2,4-di-O-(2,3,4-tri-O-pivaloyl-α-L-rhamnopyranosyl)-3,6-di-O-pivaloyl-β-D-glucopyranosyloxy]-26-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyloxy)-cholest-5-ene-16,22-dione
  参考文献：
  名称：

  Facile Conversion of Spirostan Saponin into Furostan Saponin:  Synthesis of Methyl Protodioscin and Its 26-Thio-analogue

  摘要：

  A facile approach for the conversion of a spirostan saponin into its furostan counterpart, as illustrated by the transformation of dioscin to methyl protodioscin (and its 26-thio-analogue), has been developed.

  DOI：

  10.1021/ol060594w
• 作为产物：
  描述：

  (25R)-3β-[2,4-di-O-(2,3,4-tri-O-pivaloyl-α-L-rhamnopyranosyl)-3,6-di-O-pivaloyl-β-D-glucopyranosyloxy]-5,6-epoxy-spirostan-16α-ol 在 三甲基氯硅烷 、 4 A molecular sieve 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 0.33h， 以89%的产率得到(25R)-3β-[2,4-di-O-(2,3,4-tri-O-pivaloyl-α-L-rhamnopyranosyl)-3,6-di-O-pivaloyl-β-D-glucopyranosyloxy]-26-iodo-cholest-5-ene-16,22-dione
  参考文献：
  名称：

  Facile Conversion of Spirostan Saponin into Furostan Saponin:  Synthesis of Methyl Protodioscin and Its 26-Thio-analogue

  摘要：

  A facile approach for the conversion of a spirostan saponin into its furostan counterpart, as illustrated by the transformation of dioscin to methyl protodioscin (and its 26-thio-analogue), has been developed.

  DOI：

  10.1021/ol060594w