3β-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)oxy-2α-methoxymethyloxy-olean-12-en-28-oic acid benzyl ester | 1334770-21-6

• 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: 3β-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)oxy-2α-methoxymethyloxy-olean-12-en-28-oic acid benzyl ester
• 英文别名: benzyl (4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-10-[(2R,3R,4R,5R,6R)-3-hydroxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-11-(methoxymethoxy)-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: 1334770-21-6
• 化学式: C₆₆H₈₆O₁₀
• 分子量: 1039.4
• InChiKey: GUIJOKQERXIFIQ-HATHYVCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.8
• 重原子数：
  76
• 可旋转键数：
  19
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  ethyl 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl-(1->4)-2,3-di-O-acetyl-1-thio-β-D-xylopyranoside 、 3β-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)oxy-2α-methoxymethyloxy-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 0.67h， 以79%的产率得到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-benzyl-β-D-glucopyranosyl]oxy-2α-methoxymethyloxy-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：

  2α-methoxymethyloxy-3-oxoolean-12-en-28-oic acid benzyl ester 在 sodium tetrahydroborate 、 N-碘代丁二酰亚胺 、 乙醇 、 三氟甲磺酸三甲基硅酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.33h， 生成 3β-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)oxy-2α-methoxymethyloxy-olean-12-en-28-oic acid benzyl ester 、 3β-(3,4,6-tri-O-benzyl-α-D-glucopyranosyl)oxy-2α-methoxymethyloxy-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