(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-α-D-glucopyranosyl diethyl phosphite | 1038536-90-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 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-α-D-glucopyranosyl diethyl phosphite
• CAS: 1038536-90-1
• 化学式: C₄₄H₆₉O₂₄P
• 分子量: 1012.99
• InChiKey: NVGGFEHKJMIFGE-UOCCZNCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.43
• 重原子数：
  69.0
• 可旋转键数：
  19.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  284.24
• 氢给体数：
  0.0
• 氢受体数：
  24.0

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-α-D-glucopyranosyl diethyl phosphite 、 薯蓣皂素 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.5h， 以41%的产率得到diosgenyl 2,4-di-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-3,6-di-O-pivaloyl-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
• 作为产物：
  描述：

  二乙基亚磷酰氯 、 (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 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以93%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-α-D-glucopyranosyl diethyl phosphite
  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