2α-methoxymethyloxy-3-oxoolean-12-en-28-oic acid benzyl ester | 1334770-19-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2α-methoxymethyloxy-3-oxoolean-12-en-28-oic acid benzyl ester
• CAS: 1334770-19-2
• 化学式: C₃₉H₅₆O₅
• 分子量: 604.871
• InChiKey: FXJZNHJTVVZLHD-RLKFXKHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  44.0
• 可旋转键数：
  6.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2α-methoxymethyloxy-3-oxoolean-12-en-28-oic acid benzyl ester 在 sodium tetrahydroborate 、 乙醇 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以82%的产率得到2α-methoxymethyloxy-3β-hydroxy-olean-12-en-28-oic acid benzyl ester
  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
• 作为产物：
  描述：

  2-硒吩亚磺酸,5-甲基- 、 氯甲基甲基醚 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以88%的产率得到2α-methoxymethyloxy-3-oxoolean-12-en-28-oic acid benzyl ester
  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