methyl (2S,3S,4S,5R,6R)-6-[(2S,3R,4S,5R,6R)-2-[[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bR)-11-(acetyloxymethyl)-4,4,6a,6b,8a,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-3-yl]oxy-3,4,5-triacetyloxyoxane-2-carboxylate | 161665-55-0

• 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: methyl (2S,3S,4S,5R,6R)-6-[(2S,3R,4S,5R,6R)-2-[[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bR)-11-(acetyloxymethyl)-4,4,6a,6b,8a,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-3-yl]oxy-3,4,5-triacetyloxyoxane-2-carboxylate
• CAS: 161665-55-0
• 化学式: C₅₇H₈₄O₂₀
• 分子量: 1089.28
• InChiKey: LVSJWBCHWSLUBP-OAELZQAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  77
• 可旋转键数：
  22
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  247
• 氢给体数：
  0
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  methyl (2S,3S,4S,5R,6R)-6-[(2S,3R,4S,5R,6R)-2-[[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bR)-11-(acetyloxymethyl)-4,4,6a,6b,8a,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-3-yl]oxy-3,4,5-triacetyloxyoxane-2-carboxylate 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 8.0h， 以79.7%的产率得到
  参考文献：
  名称：

  Studies on synthesis and structure-activity relationships against cytoprotective activity of triterpenoidal diglycosides with an acid saccharide, d-glucopyranosuronic acid

  摘要：

  Several triterpenoid alpha- and beta-diglycosides of oleanoic acid (1), 11-deoxoglycyrrhetic acid (4) and 11-deoxoglycyrrhetol (5) were synthesized. The synthetic diglycosides induced one or both D-glucopymanosuronic acids as sugar components. Cytoprotective activities of the diglycosides against carbon tetrachloride-induced hepatotoxicity were investigated using mice. The activities of the synthetic diglycosides were estimated by assay of aspartate transaminase and alanine transaminase, which were released from the injured hepatocytes and compared with that of glycyrrhizin (9). The beta-diglycosides of 1 and 4 showed potent activities in contrast to those of 5; none of the alpha-glycosides showed remarkable activity. Reduction of the carbonyl group (C=O) at C-11 on the C-ring of the aglycons slightly enhanced the activity over that of 9, and replacement of the carboxyl group (COOH) on the aglycons by a hydroxylmethyl group (CH2OH) drastically decreased the activity.

  DOI：

  10.1016/0223-5234(94)90073-6
• 作为产物：
  描述：

  (3beta,20beta)-3-羟基-11-氧代-齐墩果-12-烯-29-酸甲酯 在 platinum(IV) oxide 、 palladium on activated charcoal 吡啶 、 calcium sulfate 、 氢氧化钾 、 lithium aluminium tetrahydride 、 氨 、 氢气 、 silver trifluoromethanesulfonate 、 氰化汞 、 silver carbonate 、 1,1,3,3-四甲基脲 、 mercury dibromide 作用下， 以 乙醚 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 309.0h， 生成 methyl (2S,3S,4S,5R,6R)-6-[(2S,3R,4S,5R,6R)-2-[[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bR)-11-(acetyloxymethyl)-4,4,6a,6b,8a,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-3-yl]oxy-3,4,5-triacetyloxyoxane-2-carboxylate
  参考文献：
  名称：

  Studies on synthesis and structure-activity relationships against cytoprotective activity of triterpenoidal diglycosides with an acid saccharide, d-glucopyranosuronic acid

  摘要：

  Several triterpenoid alpha- and beta-diglycosides of oleanoic acid (1), 11-deoxoglycyrrhetic acid (4) and 11-deoxoglycyrrhetol (5) were synthesized. The synthetic diglycosides induced one or both D-glucopymanosuronic acids as sugar components. Cytoprotective activities of the diglycosides against carbon tetrachloride-induced hepatotoxicity were investigated using mice. The activities of the synthetic diglycosides were estimated by assay of aspartate transaminase and alanine transaminase, which were released from the injured hepatocytes and compared with that of glycyrrhizin (9). The beta-diglycosides of 1 and 4 showed potent activities in contrast to those of 5; none of the alpha-glycosides showed remarkable activity. Reduction of the carbonyl group (C=O) at C-11 on the C-ring of the aglycons slightly enhanced the activity over that of 9, and replacement of the carboxyl group (COOH) on the aglycons by a hydroxylmethyl group (CH2OH) drastically decreased the activity.

  DOI：

  10.1016/0223-5234(94)90073-6