2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl 3β-[2,3,4-tri-O-acetyl-α-L-arabinopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xylopyranosyl-(1->2)-3,4,6-tri-O-acetyl-β-D-glucopyranosyl]oxy-2α-hydroxyolean-12-en-28-oate | 1334770-37-4

• 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: 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl 3β-[2,3,4-tri-O-acetyl-α-L-arabinopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xylopyranosyl-(1->2)-3,4,6-tri-O-acetyl-β-D-glucopyranosyl]oxy-2α-hydroxyolean-12-en-28-oate
• 英文别名: [(2S,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl] (4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-10-[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-[(2S,3R,4S,5R)-3,4-diacetyloxy-5-[(2S,3R,4S,5S)-3,4,5-triacetyloxyoxan-2-yl]oxyoxan-2-yl]oxyoxan-2-yl]oxy-11-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• CAS: 1334770-37-4
• 化学式: C₇₄H₁₀₆O₃₂
• 分子量: 1507.64
• InChiKey: CKPHQSKSXIPNPU-MNUINLMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  106
• 可旋转键数：
  32
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  400
• 氢给体数：
  1
• 氢受体数：
  32

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl 3β-[2,3,4-tri-O-acetyl-α-L-arabinopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xylopyranosyl-(1->2)-3,4,6-tri-O-acetyl-β-D-glucopyranosyl]oxy-2α-hydroxyolean-12-en-28-oate 在 甲醇 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以91%的产率得到3β-[(O-α-L-arabinopyranosyl-(1->4)-O-β-D-xylopyranosyl-(1->2)-β-D-glucopyranosyl)oxy]-2α-hydroxyolean-12-en-28-oic acid α-L-rhamnopyranosyl 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：

  3β-[2,3,4-tri-O-acetyl-α-L-arabinopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xylopyranosyl-(1->2)-3,4,6-tri-O-acetyl-β-D-glucopyranosyl]oxy-2α-hydroxyolean-12-en-28-oic acid 、 2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate 在 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， 以79%的产率得到2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl 3β-[2,3,4-tri-O-acetyl-α-L-arabinopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xylopyranosyl-(1->2)-3,4,6-tri-O-acetyl-β-D-glucopyranosyl]oxy-2α-hydroxyolean-12-en-28-oate
  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