digitoxigenin 3-O-acetyl-2,6-dideoxy-β-D-ribo-hexopyranoside | 74264-36-1

• 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: digitoxigenin 3-O-acetyl-2,6-dideoxy-β-D-ribo-hexopyranoside
• 英文别名: digitoxigen 3-O-acetyl-2,6-dideoxy-β-D-ribo-hexopyranoside；[(2R,3R,4S,6R)-3-hydroxy-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: 74264-36-1
• 化学式: C₃₁H₄₆O₈
• 分子量: 546.701
• InChiKey: WXGMLPRRMCYNGD-NHJZZHOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  39
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  digitoxigenin 3-O-acetyl-2,6-dideoxy-β-D-ribo-hexopyranoside 在 tris(dibenzylideneacetone)dipalladium (0) sodium tetrahydroborate 、 cerium(III) chloride 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 11.0h， 生成 digitoxigen 3-O-acetyl-2,6-dideoxy-4-O-((2'R,5'R,6'R)-5',6'-dihydro-5'-hydroxy-6'-methyl-2H-pyran-2'-yl)-β-D-ribo-hexopyranoside
  参考文献：
  名称：

  通过钯催化的糖基化从洋地黄毒苷立体选择性合成洋地黄毒苷和洋地黄毒苷单和双指氧苷。

  摘要：

  已经开发了收敛和立体控制的三糖天然产物洋地黄毒苷的途径。该路线适合于制备洋地黄毒苷和双洋地黄毒苷。该途径的特征是钯催化的糖基化反应，还原性1,3-移位，非对映选择性二羟基化和区域选择性保护的迭代应用。天然产物洋地黄毒苷从洋地黄毒苷2和吡喃酮8a开始共分15步，或从非手性酰基呋喃开始共18步。

  DOI：

  10.1021/ol061683b
• 作为产物：
  描述：

  (5beta)-3beta-[(2,6-二脱氧-beta-D-核-己糖吡喃糖苷)氧基]-14-羟基心甾-20(22)-烯内酯 在 水 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 digitoxigenin 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

文献信息

• De Novo Approach to 2-Deoxy-β-glycosides:  Asymmetric Syntheses of Digoxose and Digitoxin¹
  作者：Maoquan Zhou、George A. O'Doherty

  DOI：10.1021/jo062534+

  日期：2007.3.1

  straightforward route to trisaccharide natural products digoxose and digitoxin has been developed. Key to this approach is the iterative application of the palladium-catalyzed glycosylation reaction, reductive 1,3-transposition, diastereoselective dihydroxylation, and regioselective protection. The first total synthesis of natural product digoxose was accomplished in 19 total steps from achiral 2-acylfuran

  已经开发出了高度对映选择性和直接的途径来制备三糖天然产物地高糖和洋地黄毒苷。该方法的关键是钯催化糖基化反应，还原性1,3-移位，非对映选择性二羟基化和区域选择性保护的迭代应用。天然产物digoxose的第一全合成是在非手性从2- acylfuran 19个总步骤完成，和洋地黄毒苷在15个步骤塑成从洋地黄毒苷开始2和吡喃酮8 β。这种灵活的合成策略还允许制备地高糖和洋地黄毒苷的单糖和二糖类似物。
• A Direct Comparison of the Anticancer Activities of Digitoxin MeON-Neoglycosides and <i>O</i>-Glycosides
  作者：Anand Krishnan V. Iyer、Maoquan Zhou、Neelam Azad、Hosam Elbaz、Leo Wang、Derek K. Rogalsky、Yon Rojanasakul、George A. O'Doherty、Joseph M. Langenhan

  DOI：10.1021/ml1000933

  日期：2010.10.14

  Digitoxin is a cardiac glycoside currently being investigated for potential use in oncology; however, an investigation of anticancer activity as a function, of oligosaccharide chain length has not yet been performed. We generated mono-, di-, and tri-O-digitoxoside derivatives, of digitoxin and compared their activities to the corresponding MeON-neoglycosides. Both classes of cardenolide derivatives display comparable oligosaccharide chain length-dependent cytotoxicity toward human cancer cell lines. Further investigation revealed that both classes of compounds induce caspase-9-mediated apoptosis in non-small cell lung cancer cells (NCI-H460). Because O-glycosides and MeON-neoglycosides share a similar mode of action, the convenience of MeON-neoglycosylation could be exploited in future SAR work to rapidly survey large numbers of carbohydrates to prioritize selected O-glycoside candidates for traditional synthesis.