diosgenyl 3-O-pivaloyl-6-O-triphenylmethyl-β-D-glucopyranoside | 848485-77-8

• 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: diosgenyl 3-O-pivaloyl-6-O-triphenylmethyl-β-D-glucopyranoside
• CAS: 848485-77-8
• 化学式: C₅₇H₇₄O₉
• 分子量: 903.209
• InChiKey: QQRPVLRRRUWYSH-SNDLIXKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.15
• 重原子数：
  66.0
• 可旋转键数：
  9.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  112.91
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  diosgenyl 3-O-pivaloyl-6-O-triphenylmethyl-β-D-glucopyranoside 、 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyltrichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以95%的产率得到diosgenyl 2,4-di-O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-3-O-pivaloyl-6-O-triphenylmethyl-β-D-glucopyranoside
  参考文献：
  名称：

  Fluorophore-Appended Steroidal Saponin (Dioscin and Polyphyllin D) Derivatives

  摘要：

  The synthesis of three fluorophore-appended derivatives of dioscin and polyphyllin D is reported herein. Starting from trillin, dansyl derivatives A-C were prepared in overall yields of 7-12% over 7-10 steps. A study of their behavior in a variety of polar solvents suggests that dansyl derivatives A-C are capable of micellar self-assembly and can maintain cytotoxicities (IC50 = 15-18 muM) against the HeLa carcinoma cell line evaluated by standard MTT assay.

  DOI：

  10.1021/ol0475616
• 作为产物：
  描述：

  地索苷 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 diosgenyl 3-O-pivaloyl-6-O-triphenylmethyl-β-D-glucopyranoside
  参考文献：
  名称：

  Fluorophore-Appended Steroidal Saponin (Dioscin and Polyphyllin D) Derivatives

  摘要：

  The synthesis of three fluorophore-appended derivatives of dioscin and polyphyllin D is reported herein. Starting from trillin, dansyl derivatives A-C were prepared in overall yields of 7-12% over 7-10 steps. A study of their behavior in a variety of polar solvents suggests that dansyl derivatives A-C are capable of micellar self-assembly and can maintain cytotoxicities (IC50 = 15-18 muM) against the HeLa carcinoma cell line evaluated by standard MTT assay.

  DOI：

  10.1021/ol0475616