methyl (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bS)-10-[(2R,3R,4R,5S,6S)-4,5-diacetyloxy-3-iodo-6-methyloxan-2-yl]oxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylate | 194344-46-2

• 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,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bS)-10-[(2R,3R,4R,5S,6S)-4,5-diacetyloxy-3-iodo-6-methyloxan-2-yl]oxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylate
• CAS: 194344-46-2
• 化学式: C₄₁H₆₁IO₉
• 分子量: 824.834
• InChiKey: FOKXABMXXGJMLG-SFVBARSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  51
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bS)-10-[(2R,3R,4R,5S,6S)-4,5-diacetyloxy-3-iodo-6-methyloxan-2-yl]oxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylate 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 192.0h， 以89.6%的产率得到(2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bS)-10-((2R,4S,5S,6S)-4,5-Diacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-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 methyl ester
  参考文献：
  名称：

  Stereoselective synthesis of triterpene and steroid 2-deoxy-α-glycosides using iodonium dicollidine perchlorate

  摘要：

  2-Deoxy-alpha-glycosides of oleonane type triterpene alcohols and deoxycholic acid were synthesized by glycosylation with glycal acetates in the presence of iodonium dicollidine perchlorate followed by deiodination and deprotection.

  DOI：

  10.1007/bf02495419
• 作为产物：
  描述：

  (3β,18α)-methyl 3-hydroxy-11-oxoolean-12-30-oate 、 3,4-二-O-乙酰-1,5-酐-2,6-双脱氧-L-阿拉伯-己-1-糖醇 在 iodonium di(2,4,6-trimethylpyridine) perchlorate 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以85%的产率得到methyl (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bS)-10-[(2R,3R,4R,5S,6S)-4,5-diacetyloxy-3-iodo-6-methyloxan-2-yl]oxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylate
  参考文献：
  名称：

  Stereoselective synthesis of triterpene and steroid 2-deoxy-α-glycosides using iodonium dicollidine perchlorate

  摘要：

  2-Deoxy-alpha-glycosides of oleonane type triterpene alcohols and deoxycholic acid were synthesized by glycosylation with glycal acetates in the presence of iodonium dicollidine perchlorate followed by deiodination and deprotection.

  DOI：

  10.1007/bf02495419