3-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-[(2R,4S,5R,6R)-4,5-bis[[tert-butyl(diphenyl)silyl]oxy]-6-methyloxan-2-yl]oxy-14-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one | 1345697-42-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-[(2R,4S,5R,6R)-4,5-bis[[tert-butyl(diphenyl)silyl]oxy]-6-methyloxan-2-yl]oxy-14-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
• CAS: 1345697-42-8
• 化学式: C₆₁H₈₀O₇Si₂
• 分子量: 981.473
• InChiKey: ZTDOKEKVKHNLCB-SHSFCNQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.65
• 重原子数：
  70
• 可旋转键数：
  13
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  洋地黄毒苷 在 trifluoromethanesulfonyloxy(triphenylphosphine)gold(I) 、 硫酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 3-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-[(2R,4S,5R,6R)-4,5-bis[[tert-butyl(diphenyl)silyl]oxy]-6-methyloxan-2-yl]oxy-14-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one 、
  参考文献：
  名称：

  Assembly of Digitoxin by Gold(I)-Catalyzed Glycosidation of Glycosyl o-Alkynylbenzoates

  摘要：

  Digitoxin, a clinically important cardiac trisactharicle, was assembled efficiently from digitoxigenin and 3,4-di-O-tert-butyldiphenylsilyl-D-digitoxosyl o-cyclopropylethynyl-benzoate in 9 steps and 52% overall yield via alternate glycosylation and protecting group manipulation. The present synthesis showcases the advantage of the gold(I)-catalyzed glycosylation protocol in the synthesis of glycoconjugates containing acid-labile 2-deoxysugar linkages.

  DOI：

  10.1021/jo201850z