3"',4"'-di-O-acetyl digitoxin | 25876-27-1

• 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"',4"'-di-O-acetyl digitoxin
• 英文别名: digitoxin 3"',4"'-diacetate；O-Acetyl-digitoxin-α
• CAS: 25876-27-1
• 化学式: C₄₅H₆₈O₁₅
• 分子量: 849.026
• InChiKey: IKUXTVKXORXQEW-LJIOBJEESA-N

物化性质

• 沸点：
  903.4±65.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  60.0
• 可旋转键数：
  9.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  194.97
• 氢给体数：
  3.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  3"',4"'-di-O-acetyl digitoxin 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 洋地黄毒苷
  参考文献：
  名称：

  Convergent Synthesis of Digitoxin: Stereoselective Synthesis and Glycosylation of the Digoxin Trisaccharide Glycal This research was supported by the U.S. National Institutes of Health (CA-59703). F.E.M. also thanks Novartis Pharmaceuticals for unrestricted additional funding (Grant Program for the Support of Academic Research in Synthetic Organic Chemistry).

  摘要：

  DOI：

  10.1002/1521-3773(20011001)40:19<3653::aid-anie3653>3.0.co;2-w
• 作为产物：
  描述：

  Benzoic acid (1R,2R,3S)-2-[(2S,4S,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pent-4-ynyl ester 在 六羰基钨 1-甲基吡咯烷 、 三乙烯二胺 、 4-二甲氨基吡啶 、 氟化铵 、 四丁基氟化铵 、 氢溴酸 、 二异丁基氢化铝 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 6.0h， 生成 3"',4"'-di-O-acetyl digitoxin
  参考文献：
  名称：

  Convergent Synthesis of Digitoxin: Stereoselective Synthesis and Glycosylation of the Digoxin Trisaccharide Glycal This research was supported by the U.S. National Institutes of Health (CA-59703). F.E.M. also thanks Novartis Pharmaceuticals for unrestricted additional funding (Grant Program for the Support of Academic Research in Synthetic Organic Chemistry).

  摘要：

  DOI：

  10.1002/1521-3773(20011001)40:19<3653::aid-anie3653>3.0.co;2-w

文献信息

• Recent advances in the synthesis of 2-deoxy-glycosides
  作者：Dianjie Hou、Todd L. Lowary

  DOI：10.1016/j.carres.2009.07.013

  日期：2009.10

  Glycosides of 2-deoxy-sugars, monosaccharides in which the hydroxyl group at C-2 is replaced with a hydrogen atom, occur widely in natural products and therefore have been the subject of intense synthetic activity. The report summarizes recent advances in this area, with a particular focus on work published since an earlier review on the topic, in 2000 (Marzabadi, C. H.: Franck, R. W. Tetrahedron 2000, 56, 8385-8417). (C) 2009 Elsevier Ltd. All rights reserved.
• Perfectly regioselective acylation of a cardiac glycoside, digitoxin, via catalytic amplification of the intrinsic reactivity
  作者：Keisuke Yoshida、Takumi Furuta、Takeo Kawabata

  DOI：10.1016/j.tetlet.2010.07.036

  日期：2010.9

  Organocatalytic regioselective acylation of digitoxin has been developed. This method provides the 4'''-O-manoacylate as the sole product without the concomitant formation of diacylates. The extremely high regioselectivity was assumed to be the result from the combined effects of the high intrinsic reactivity of C(4''')-OH and catalyst-promoted regioselective acylation of the same hydroxy group. (C) 2010 Elsevier Ltd. All rights reserved.