[(2R,3R,4R,5R,6S)-3,4-dibenzoyloxy-6-ethylsulfanyl-5-hydroxyoxan-2-yl]methyl benzoate | 956937-64-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4R,5R,6S)-3,4-dibenzoyloxy-6-ethylsulfanyl-5-hydroxyoxan-2-yl]methyl benzoate
• CAS: 956937-64-7
• 化学式: C₂₉H₂₈O₈S
• 分子量: 536.603
• InChiKey: SXHICFCNNPHJHW-LPSUVQJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  134
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4R,5R,6S)-3,4-dibenzoyloxy-6-ethylsulfanyl-5-hydroxyoxan-2-yl]methyl benzoate 、 2α-methoxymethyloxy-3β-hydroxy-olean-12-en-28-oic acid benzyl ester 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 、
  参考文献：
  名称：

  Synthesis of stryphnoside A, a triterpene saponin isolated from the pericarps of Stryphnodendron fissuratum

  摘要：

  Stryphnoside A, alpha-L-rhamnopyranosyl 3 beta-O-[alpha-L-arabinopyranosyl-(1 -> 4)-beta-D-xylopyranosyl-(1 -> 2)-beta-D-glucopyranosyl]-2 alpha-hydroxyolean-12-en-28-oate, has been synthesized in 11 steps in 15% overall yield starting from the naturally abundant oleanolic acid. Condensation of a partially protected glucopyranosyl donor and 2 alpha, 3 beta-dihydroxyolean-12-en-28-oic acid derivative using inverse glycosylation procedure has significantly simplified the target saponin synthesis. Stryphnoside A exhibited weak cytotoxic activities against tumor cells HeLa, A549, and HepG2 with IC50 at mM level. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.06.006

文献信息

• Synthesis of stryphnoside A, a triterpene saponin isolated from the pericarps of Stryphnodendron fissuratum
  作者：Xun Lv、Shouyi Yu、Jing Wang、Yuguo Du

  DOI：10.1016/j.carres.2011.06.006

  日期：2011.9

  Stryphnoside A, alpha-L-rhamnopyranosyl 3 beta-O-[alpha-L-arabinopyranosyl-(1 -> 4)-beta-D-xylopyranosyl-(1 -> 2)-beta-D-glucopyranosyl]-2 alpha-hydroxyolean-12-en-28-oate, has been synthesized in 11 steps in 15% overall yield starting from the naturally abundant oleanolic acid. Condensation of a partially protected glucopyranosyl donor and 2 alpha, 3 beta-dihydroxyolean-12-en-28-oic acid derivative using inverse glycosylation procedure has significantly simplified the target saponin synthesis. Stryphnoside A exhibited weak cytotoxic activities against tumor cells HeLa, A549, and HepG2 with IC50 at mM level. (C) 2011 Elsevier Ltd. All rights reserved.