methyl 2,3,4-tri-O-acetyl-1-O-(17-oxoandrost-5-en-3β-yl)-β-D-glucopyranosiduronate | 121707-84-4

• 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: methyl 2,3,4-tri-O-acetyl-1-O-(17-oxoandrost-5-en-3β-yl)-β-D-glucopyranosiduronate
• 英文别名: O²,O³,O⁴-triacetyl-O¹-(17-oxo-androst-5-en-3β-yl)-β-D-glucopyranuronic acid methyl ester；O²,O³,O⁴-Triacetyl-O¹-(17-oxo-androst-5-en-3β-yl)-β-D-glucopyranuronsaeure-methylester；methyl (2S,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl]oxy]oxane-2-carboxylate
• CAS: 121707-84-4
• 化学式: C₃₂H₄₄O₁₁
• 分子量: 604.695
• InChiKey: ORJMEIUSIUSLNZ-NLZJITPRSA-N

物化性质

• 熔点：
  194-195 °C
• 沸点：
  640.6±55.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-acetyl-1-O-(17-oxoandrost-5-en-3β-yl)-β-D-glucopyranosiduronate 在 N-羟基邻苯二甲酰亚胺 、 氧气 、 sodium methylate 、 过氧化苯甲酰 作用下， 以 甲醇 、 乙酸乙酯 、 丙酮 为溶剂， 反应 3.0h， 生成 methyl 1-O-(7,17-dioxoandrost-5-en-3β-yl)-β-D-glucopyranosiduronate
  参考文献：
  名称：

  Ergosteroids IV: synthesis and biological activity of steroid glucuronosides, ethers, and alkylcarbonates

  摘要：

  The 7-oxo derivative of dehydroepiandrosterone is more active than the parent steroid and is devoid of adverse side effects in rats, monkeys and humans. In anticipation of possible therapeutic use we have sought more active, longer lasting forms of 7-oxo- and 7 beta -hydroxydehydroepiandrosterones. The 7-oxo- and 7-hydroxy steroids have been converted to glucuronides, ethers and carbonate esters. The syntheses of these compounds are described and their ability to induce the formation of liver thermogenic enzymes when fed to rats is reported. Some of the new derivatives were found to be somewhat more effective than the equimolar amounts of 7-oxo-DHEA with which they were compared in each experiment. (C) 2001 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(00)00234-8
• 作为产物：
  描述：

  去氢表雄酮 、 乙酰溴-Alpha-D-葡萄糖酮酸甲基酯 在 乙醚 、 silver carbonate 作用下， 生成 methyl 2,3,4-tri-O-acetyl-1-O-(17-oxoandrost-5-en-3β-yl)-β-D-glucopyranosiduronate
  参考文献：
  名称：

  Pelzer, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1959, vol. 314, p. 234,239

  摘要：

  DOI：

文献信息

• Schapiro, Biochemical Journal, 1939, vol. 33, p. 385,387
  作者：Schapiro

  DOI：——

  日期：——
• D-Glucopyranosiduronates. I. Steroidyl-β-D-glucopyranuronosides^1,2
  作者：Herbert H. Wotiz、Erika Smakula、Norman N. Lichtin、Jehaudah H. Leftin

  DOI：10.1021/ja01516a046

  日期：1959.4