methyl 3-O-(3,4,6-tri-O-acetyl-2-deoxy-α-D-lyxo-hexopyranosyl)-11-deoxo-18β-glycyrrhetinate | 189222-53-5

• 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 3-O-(3,4,6-tri-O-acetyl-2-deoxy-α-D-lyxo-hexopyranosyl)-11-deoxo-18β-glycyrrhetinate
• 英文别名: methyl (2S,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bR)-10-[(2S,4R,5R,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-2,4a,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-2-carboxylate
• CAS: 189222-53-5
• 化学式: C₄₃H₆₆O₁₀
• 分子量: 742.991
• InChiKey: VMKSVAQKGPKOTF-VJCCGILDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  53
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl 3-O-(3,4,6-tri-O-acetyl-2-deoxy-α-D-lyxo-hexopyranosyl)-11-deoxo-18β-glycyrrhetinate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 以68%的产率得到(2S,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bR)-10-((2S,4R,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2,4a,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydro-picene-2-carboxylic acid
  参考文献：
  名称：

  Stereoselective synthesis of triterpene 2-deoxy-α-d-lyxo-hexopyranosides

  摘要：

  2-Deoxy-alpha-D-lyxo-hexopyranosides of 18 beta-glycyrrhetic acid, its 11-deoxo derivative and allobetulin were synthesized by glycosylation of oleonane-type triterpene alcohols with D-galactal acetate in the presence of N-iodosuccinimide followed by deiodination and deprotection.

  DOI：

  10.1007/bf02495418
• 作为产物：
  描述：

  D-三乙酰半乳糖烯 在 palladium on activated charcoal N-碘代丁二酰亚胺 、 4 A molecular sieve 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 反应 310.0h， 生成 methyl 3-O-(3,4,6-tri-O-acetyl-2-deoxy-α-D-lyxo-hexopyranosyl)-11-deoxo-18β-glycyrrhetinate
  参考文献：
  名称：

  Stereoselective synthesis of triterpene 2-deoxy-α-d-lyxo-hexopyranosides

  摘要：

  2-Deoxy-alpha-D-lyxo-hexopyranosides of 18 beta-glycyrrhetic acid, its 11-deoxo derivative and allobetulin were synthesized by glycosylation of oleonane-type triterpene alcohols with D-galactal acetate in the presence of N-iodosuccinimide followed by deiodination and deprotection.

  DOI：

  10.1007/bf02495418

文献信息

• Baltina; Flekhter; Vasil'eva, Russian Journal of Bioorganic Chemistry, 1997, vol. 23, # 6, p. 474 - 480
  作者：Baltina、Flekhter、Vasil'eva、Davydova、Ismagilova、Zarudii、Tolstikov

  DOI：——

  日期：——
• Stereoselective synthesis of triterpene 2-deoxy-α-d-lyxo-hexopyranosides
  作者：L. A. Baltina、O. B. Flekhter、E. V. Vasil'eva、G. A. Tolstikov

  DOI：10.1007/bf02495418

  日期：1997.3

  2-Deoxy-alpha-D-lyxo-hexopyranosides of 18 beta-glycyrrhetic acid, its 11-deoxo derivative and allobetulin were synthesized by glycosylation of oleonane-type triterpene alcohols with D-galactal acetate in the presence of N-iodosuccinimide followed by deiodination and deprotection.