(digitoxigenin-3β-yl)-β-D-quinovoside | 40950-57-0

• 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-3β-yl)-β-D-quinovoside
• 英文别名: digitoxigenin-3-O-β-d-quinovoside；(digitoxigenin-3beta-yl)-beta-D-quinovoside；3-[(3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
• CAS: 40950-57-0
• 化学式: C₂₉H₄₄O₈
• 分子量: 520.664
• InChiKey: WQMLFJWIKARBFW-QYLLKCSRSA-N

物化性质

• 沸点：
  694.6±55.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  37
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  D-Fucose 在 吡啶 、 2,4,6-三甲基吡啶 、 lead(IV) acetate 、 sodium hydroxide 、 Dowex 1X₈ (HCO₃^-) 、 水 、 氢溴酸 、 silver carbonate 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 160.5h， 生成 (digitoxigenin-3β-yl)-β-D-quinovoside
  参考文献：
  名称：

  Synthesis of Uridine 5′-(α-D-Fucopyranosyl Diphosphate) and (Digitoxigenin-3β-yl)-β-D-Fucopyranoside and Enzymatic β-D-Fucosylation of Cardenolide Aglycones in Digitalis lanata1

  摘要：

  The phosphorylation of 2,3,4-tri-O-acetyl-alpha-D-fucopyranose with o-phenylene phosphochloridate yielded alpha-D-fucopyranosyl phosphate which was used for condensation with uridine 5'-monophosphomorpholidate to give uridine 5'-(alpha-D-fucopyranosyl diphosphate) (UDP-alpha-D-fucose). A crude enzyme preparation from young leaves of Digitalis lanata EHRH has been shown to catalyze the transfer of D-fucose from synthetic UDP-alpha-D-fucose to cardenolide aglycones, such as digitoxigenin. The reaction product was identified and characterized by chemical synthesis, HPLC, and spectral methods as the 3 beta-O-beta-D-fucopyranoside of digitoxigenin (digiproside). (C) 1994 Academic Press, Inc.

  DOI：

  10.1006/bioo.1994.1012

文献信息

• Preparation of 3-(6-Deoxy-β-D-glucopyranosyloxy) and 3-(6-Deoxy-α-L-mannopyranosyloxy)androstane Derivatives with Unsaturated Side Chain in Position 17β
  作者：Hana Chodounská、Vladimír Pouzar

  DOI：10.1135/cccc19933000

  日期：——

  In our previous papers we described the preparation of 3-β-D-glucopyranosyloxy) and 3-β-D-galactopyranosyloxy) derivatives of steroids with an α,β-unsaturated ester chain in position 17β of androstane skeleton. In conection with this project we have studied silver silicate promoted glycosylation of some of above mentioned steroidal derivatives with 2,3,4-tri-O-acetyl-6-deoxy-α-D-glucopyranosyl bromide and 2,3,4-tri-O-acetyl-6-deoxy-α-L-mannopyranosyl bromide.

  在我们之前的论文中，我们描述了制备类固醇的3-β-D-葡萄糖苷基）和3-β-D-半乳糖苷基）衍生物的方法，这些衍生物在雄甾烷骨架的17β位置具有α，β-不饱和酯链。在这个项目中，我们研究了银硅酸盐促进的一些上述类固醇衍生物与2,3,4-三-O-乙酰基-6-去氧-α-D-葡萄糖苷溴化物和2,3,4-三-O-乙酰基-6-去氧-α-L-甘露糖苷溴化物的糖基化反应。
• Synthesis of Uridine 5′-(α-D-Fucopyranosyl Diphosphate) and (Digitoxigenin-3β-yl)-β-D-Fucopyranoside and Enzymatic β-D-Fucosylation of Cardenolide Aglycones in Digitalis lanata1
  作者：T. Faust、C. Theurer、K. Eger、W. Kreis

  DOI：10.1006/bioo.1994.1012

  日期：1994.6

  The phosphorylation of 2,3,4-tri-O-acetyl-alpha-D-fucopyranose with o-phenylene phosphochloridate yielded alpha-D-fucopyranosyl phosphate which was used for condensation with uridine 5'-monophosphomorpholidate to give uridine 5'-(alpha-D-fucopyranosyl diphosphate) (UDP-alpha-D-fucose). A crude enzyme preparation from young leaves of Digitalis lanata EHRH has been shown to catalyze the transfer of D-fucose from synthetic UDP-alpha-D-fucose to cardenolide aglycones, such as digitoxigenin. The reaction product was identified and characterized by chemical synthesis, HPLC, and spectral methods as the 3 beta-O-beta-D-fucopyranoside of digitoxigenin (digiproside). (C) 1994 Academic Press, Inc.