methyl 3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-iodo-α-D-talopyranosyl)-11-deoxo-18β-glycyrrhetinate | 194277-30-0

• 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 3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-iodo-α-D-talopyranosyl)-11-deoxo-18β-glycyrrhetinate
• 英文别名: methyl (2S,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bR)-10-[(2S,3S,4S,5S,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-iodooxan-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: 194277-30-0
• 化学式: C₄₃H₆₅IO₁₀
• 分子量: 868.888
• InChiKey: YZLBPGJIJCBKCA-XMTRCRPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  54
• 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-2-iodo-α-D-talopyranosyl)-11-deoxo-18β-glycyrrhetinate 在 palladium on activated charcoal 氢氧化钾 、 氢气 、 三乙胺 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 252.0h， 生成 (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：

  methyl 3β-hydroxy-18β-olean-12-en-30-oate 、 D-三乙酰半乳糖烯 在 N-碘代丁二酰亚胺 、 4 A molecular sieve 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 70.0h， 以54%的产率得到methyl 3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-iodo-α-D-talopyranosyl)-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：——