4-tolyl 3,6-di-O-pivaloyl-1-thio-β-D-glucopyranoside | 1038536-85-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-tolyl 3,6-di-O-pivaloyl-1-thio-β-D-glucopyranoside
• CAS: 1038536-85-4
• 化学式: C₂₃H₃₄O₇S
• 分子量: 454.585
• InChiKey: KHVAAKWEWOYQJN-QQXKLLMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.08
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  102.29
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl trichloroacetimidate 、 4-tolyl 3,6-di-O-pivaloyl-1-thio-β-D-glucopyranoside 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以55%的产率得到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
  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