evomonoside | 63700-70-9

• 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: evomonoside
• 英文别名: 3-[(3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-3-[(2R,3R,4S,5R,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: 63700-70-9
• 化学式: C₂₉H₄₄O₈
• 分子量: 520.664
• InChiKey: WQMLFJWIKARBFW-BEVFCYNPSA-N

物化性质

• 熔点：
  147-152 °C(Solv: methanol (67-56-1))
• 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

• 作为反应物：
  描述：

  evomonoside 、 乙酸酐 在 吡啶 作用下， 生成 tri-O-acetyl-digiproside
  参考文献：
  名称：

  Satoh et al., Pharmaceutical Bulletin, 1956, vol. 4, p. 284,288

  摘要：

  DOI：
• 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 evomonoside
  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

• Synthesis of cardenolide glycosides and putative biosynthetic precursors of cardenolide glycosides
  作者：Melitta Luta、Andreas Hensel、Wolfgang Kreis

  DOI：10.1016/s0039-128x(97)00118-9

  日期：1998.1

  glycosylation of steroids was established using a modified Koenigs-Knorr procedure. Peracetylated beta-glycosides were synthesized by reaction of cardenolides, various pregnanes and 23-nor-5,20(22)E-choldienic acid at room temperature with the peracetylated 1-bromo derivatives of D-glucose, D-galactose, D-fucose and cellobiose. Subsequent deprotection was performed by alkaline hydrolysis with sodium methoxide

  使用改良的 Koenigs-Knorr 程序建立了一种快速有效的类固醇糖基化程序。全乙酰化β-糖苷是通过cardenolides、各种孕烷和23-nor-5,20(22)E-胆二烯酸在室温下与D-葡萄糖、D-半乳糖、D-岩藻糖的过乙酰化1-溴衍生物反应合成的和纤维二糖。随后通过甲醇钠碱水解进行脱保护。各个糖苷的结构通过NMR技术确定。完整的方案被证明在所有阶段对糖部分和甾体核都是非破坏性的。Cardenolides 的 γ-不饱和内酯环显示保持完整，没有观察到 C-14 不饱和化合物的形成。
• Okano, Pharmaceutical Bulletin, 1957, vol. 5, p. 279,281
  作者：Okano

  DOI：——

  日期：——
• 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.
• Satoh et al., Pharmaceutical Bulletin, 1956, vol. 4, p. 284,288
  作者：Satoh et al.

  DOI：——

  日期：——