(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1->4)-[(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1->2)]-3,6-di-O-pivaloyl-1-thio-α-D-glucopyranoside | 1038536-88-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1->4)-[(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1->2)]-3,6-di-O-pivaloyl-1-thio-α-D-glucopyranoside
• 英文别名: Rha2Ac3Ac4Ac(a1-2)[Rha2Ac3Ac4Ac(a1-4)][pivaloyl(-3)][pivaloyl(-6)]a-Glc；[(2R,3R,4S,5R,6S)-4-(2,2-dimethylpropanoyloxy)-6-hydroxy-3,5-bis[[(2S,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxy]oxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 1038536-88-7
• 化学式: C₄₀H₆₀O₂₂
• 分子量: 892.903
• InChiKey: AYDKYQUAPDSSPE-LQMPUPTISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  62.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  276.78
• 氢给体数：
  1.0
• 氢受体数：
  22.0

反应信息

• 作为反应物：
  描述：

  (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1->4)-[(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1->2)]-3,6-di-O-pivaloyl-1-thio-α-D-glucopyranoside 、 三氯乙腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到
  参考文献：
  名称：

  Efficient synthesis of α- and β-chacotriosyl glycosides using appropriate donors, and their cytotoxic activity

  摘要：

  Natural steroidal glycosides containing alpha-L-rhamnopyranosyl-(1 -> 4)-[alpha-L-rhamnopyranosyl-(1 -> 2)]-beta-D-glucopyranose (chacotriose) at the oligosaccharide moiety exhibit anti-cancer and anti-herpes activities. To investigate the structure-Activity relationships of the aglycone parts of chacotriosides, we developed a synthesis method for chacotriosyl glycosides having various aglycones. In the process, it was revealed that alpha-chacotriosyl glycosides could be obtained mainly by using a trichloroacetimidate donor, while beta-chacotriosyl glycosides were afforded by using phosphite and phosphate donors. In cytotoxicity tests using the A549 and HepG2 cell lines, naturally occurring beta-chacotriosyl diosgenin and cholestanol exhibited higher activities than the corresponding alpha-chacotriosyl glycosides. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.02.012
• 作为产物：
  描述：

  4-tolyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1->4)-[(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1->2)]-3,6-di-O-pivaloyl-1-thio-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以62%的产率得到(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1->4)-[(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1->2)]-3,6-di-O-pivaloyl-1-thio-α-D-glucopyranoside
  参考文献：
  名称：

  Efficient synthesis of α- and β-chacotriosyl glycosides using appropriate donors, and their cytotoxic activity

  摘要：

  Natural steroidal glycosides containing alpha-L-rhamnopyranosyl-(1 -> 4)-[alpha-L-rhamnopyranosyl-(1 -> 2)]-beta-D-glucopyranose (chacotriose) at the oligosaccharide moiety exhibit anti-cancer and anti-herpes activities. To investigate the structure-Activity relationships of the aglycone parts of chacotriosides, we developed a synthesis method for chacotriosyl glycosides having various aglycones. In the process, it was revealed that alpha-chacotriosyl glycosides could be obtained mainly by using a trichloroacetimidate donor, while beta-chacotriosyl glycosides were afforded by using phosphite and phosphate donors. In cytotoxicity tests using the A549 and HepG2 cell lines, naturally occurring beta-chacotriosyl diosgenin and cholestanol exhibited higher activities than the corresponding alpha-chacotriosyl glycosides. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.02.012