digitoxigenin 4''-O-tert-butyldiphenylsilyl-2'',3'',6''-trideoxy-β-D-erythro-hex-2-enopyranosyl-(1->4)-3'-O-acetyl-2',6'-dideoxy-β-D-ribo-hexopyranoside | 1345697-48-4

• 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: digitoxigenin 4''-O-tert-butyldiphenylsilyl-2'',3'',6''-trideoxy-β-D-erythro-hex-2-enopyranosyl-(1->4)-3'-O-acetyl-2',6'-dideoxy-β-D-ribo-hexopyranoside
• 英文别名: [(2R,3R,4S,6R)-3-[[(2R,3S,6S)-3-[tert-butyl(diphenyl)silyl]oxy-2-methyl-3,6-dihydro-2H-pyran-6-yl]oxy]-6-[[(3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-2-methyloxan-4-yl] acetate
• CAS: 1345697-48-4
• 化学式: C₅₃H₇₂O₁₀Si
• 分子量: 897.234
• InChiKey: GYQNKTQEQBRPJG-PKFSLFOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.33
• 重原子数：
  64
• 可旋转键数：
  12
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  digitoxigenin 3-O-acetyl-2,6-dideoxy-β-D-ribo-hexopyranoside 、 3,4-di-O-tert-butyldiphenylsilyl-2,6-dideoxy-D-ribo-hexopyranosyl o-cyclopropylethynylbenzoate 在 trifluoromethanesulfonyloxy(triphenylphosphine)gold(I) 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以64%的产率得到digitoxigenin 4''-O-tert-butyldiphenylsilyl-2'',3'',6''-trideoxy-β-D-erythro-hex-2-enopyranosyl-(1->4)-3'-O-acetyl-2',6'-dideoxy-β-D-ribo-hexopyranoside
  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