(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[[(3aR,5S,6S,7R,7aR)-6,7-diacetyloxy-2,5-dimethyl-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-2-yl]oxy]-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid | 1221152-35-7

• 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: (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[[(3aR,5S,6S,7R,7aR)-6,7-diacetyloxy-2,5-dimethyl-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-2-yl]oxy]-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• CAS: 1221152-35-7
• 化学式: C₄₂H₆₄O₁₀
• 分子量: 728.964
• InChiKey: XPUQDBRXKQJOIV-NPUJQOBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  52
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-L-rhamnopyranosyl ortho-hexynylbenzoate 、 齐墩果酸 在 2,6-二叔丁基吡啶 、 trifluoromethanesulfonyloxy(triphenylphosphine)gold(I) 作用下， 以 二氯甲烷 为溶剂， 以63%的产率得到(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[[(3aR,5S,6S,7R,7aR)-6,7-diacetyloxy-2,5-dimethyl-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-2-yl]oxy]-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
  参考文献：
  名称：

  Chemoselective glycosylation of carboxylic acid with glycosyl ortho-hexynylbenzoates as donors

  摘要：

  The gold(I)-catalyzed glycosylation of acid alcohols with glycosyl ortho-hexynylbenzoates in the presence of BF3 center dot Et2O and DBU provided the corresponding ester glycosides chemoselectively in high yield; while with DTBP as an additive instead, orthoester formation with the alcohol was effected selectively. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.01.039