tetrahydrocortisone 3-glucuronide | 26312-91-4

• 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: tetrahydrocortisone 3-glucuronide
• 英文别名: Tetrahydrocortisone 3-Glucuronide；(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[[(3R,5R,8S,9S,10S,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-11-oxo-2,3,4,5,6,7,8,9,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxane-2-carboxylic acid
• CAS: 26312-91-4
• 化学式: C₂₇H₄₀O₁₁
• 分子量: 540.608
• InChiKey: QUOCEDQXFGCYTL-WPIYVXEUSA-N

物化性质

• 沸点：
  768.8±60.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  38
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  191
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  tetrahydrocortisone 3-glucuronide 生成 四氢可的松
  参考文献：
  名称：

  C-3 glucosiduronates of metabolites of adrenal steroids

  摘要：

  On treatment with methyl 2,3,4-tri-O-acetyl-1-bromo-1-deoxy-alpha-D-glucuronate and silver carbonate, tetrahydrocortisone 21-acetate gave the corresponding 3-glucosiduronate triacetyl methyl ester. This product was converted into the 20-semicarbazone which, by treatment with alkali to hydrolyze the ester functions and acid to hydrolyze the semicarbazone moiety, gave tetrahydrocortisone 3-glucosiduronic acid. The acid was converted into the crystalline barium salt and into the methyl ester. An analogous series of reactions was carried out on tetrahydrocortexolone 21-acetate. Treatment of the 20-semicarbazone of tetrahydrocortisone 3-glucosiduronic acid with potassium borohydride reduced the 11-oxo function to an 11 beta hydroxyl group; acid-catalyzed removal of the semicarbazone group produced tetrahydrocortisol 3-glucosiduronic acid which also was obtained as the barium salt and the methyl ester.

  DOI：

  10.1016/0039-128x(82)90110-6
• 作为产物：
  描述：

  醋酸氢化可的松 在 palladium on activated charcoal 、 Raney nickel (W-2) 咪唑 、 氢氧化钾 、 硫酸 、 氢气 、 silver carbonate 、 pyridinium chlorochromate 作用下， 以 1,4-二氧六环 、 吡啶 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 51.5h， 生成 tetrahydrocortisone 3-glucuronide
  参考文献：
  名称：

  Synthesis of haptens for use in immunoassays of tetrahydrocortisol, tetrahydrocortisone and their glucuronides.

  摘要：

  为了开发特异而灵敏的免疫测定方法，我们合成了四氢可的松和四氢可的松的羧化衍生物。这些皮质类固醇的 3-半琥珀酸酯（23，27）、21-半琥珀酸酯（8，14）、3-半戊二酸酯（24，28）和 21-半戊二酸酯（9，15）的制备是从皮质醇 21-乙酸酯（1）开始的。此外，还制备了四氢可的松单葡糖醛酸盐（36、38）和四氢可的松单葡糖醛酸盐（37、39）。

  DOI：

  10.1248/cpb.30.2110

文献信息

• A novel synthesis of tetrahydrocortisone 3-glucuronide
  作者：Yan Zhang、Suqing Zhang、Rui Li、Jingshan Shen、Xiangrui Jiang、Haji A. Aisa

  DOI：10.1080/07328303.2021.2023559

  日期：2022.1.2

  Abstract A new route for the synthesis of tetrahydrocortisone 3-glucuronide has been developed with cortisone acetate as a starting material. The key step was using lithium tri-tert-butoxyaluminum hydride to reduce the C-3 carbonyl group of 5β-dihydrocortisone acetate (8) to provide 3α-5β-tetrahydrocortisone acetate (5). Then, Koenig–Knorr method was used for glycosylation with glycosyl bromide as

  摘要 以醋酸可的松为起始原料，开发了一条合成四氢可的松 3-葡糖苷酸的新路线。关键步骤是使用氢化三叔丁氧基铝锂还原 5 β - 二氢可的松醋酸酯 (8) 的 C-3 羰基，得到 3 α -5 β -醋酸四氢可的松 (5)。然后，采用 Koenig-Knorr 法进行糖基化，以溴化糖为供体，碳酸镉为促进剂，4Å 分子筛为脱水剂，得到所需产物的高收率。与文献报道的相比，新路线更短，产率更高。
• C-3 glucosiduronates of metabolites of adrenal steroids
  作者：R.Mattox Vernon、June E. Goodrich、Albert N. Nelson

  DOI：10.1016/0039-128x(82)90110-6

  日期：1982.7

  On treatment with methyl 2,3,4-tri-O-acetyl-1-bromo-1-deoxy-alpha-D-glucuronate and silver carbonate, tetrahydrocortisone 21-acetate gave the corresponding 3-glucosiduronate triacetyl methyl ester. This product was converted into the 20-semicarbazone which, by treatment with alkali to hydrolyze the ester functions and acid to hydrolyze the semicarbazone moiety, gave tetrahydrocortisone 3-glucosiduronic acid. The acid was converted into the crystalline barium salt and into the methyl ester. An analogous series of reactions was carried out on tetrahydrocortexolone 21-acetate. Treatment of the 20-semicarbazone of tetrahydrocortisone 3-glucosiduronic acid with potassium borohydride reduced the 11-oxo function to an 11 beta hydroxyl group; acid-catalyzed removal of the semicarbazone group produced tetrahydrocortisol 3-glucosiduronic acid which also was obtained as the barium salt and the methyl ester.
• Synthesis of haptens for use in immunoassays of tetrahydrocortisol, tetrahydrocortisone and their glucuronides.
  作者：HIROSHI HOSODA、KEIKO SAITO、YUKO ITO、HIROMITSU YOKOHAMA、KAZUO ISHII、TOSHIO NAMBARA

  DOI：10.1248/cpb.30.2110

  日期：——

  In order to develop specific and sensitive immunoassays, carboxylated derivatives of tetrahydrocortisol and tetrahydrocortisone were synthesized. The preparation of the 3-hemisuccinates (23, 27), 21-hemisuccinates (8, 14), 3-hemiglutarates (24, 28), and 21-hemiglutarates (9, 15) of these corticosteroids was carried out starting from cortisol 21-acetate (1). Tetrahydrocortisol monoglucuronides (36, 38) and tetrahydrocortisone monoglucuronides (37, 39) were also prepared.

  为了开发特异而灵敏的免疫测定方法，我们合成了四氢可的松和四氢可的松的羧化衍生物。这些皮质类固醇的 3-半琥珀酸酯（23，27）、21-半琥珀酸酯（8，14）、3-半戊二酸酯（24，28）和 21-半戊二酸酯（9，15）的制备是从皮质醇 21-乙酸酯（1）开始的。此外，还制备了四氢可的松单葡糖醛酸盐（36、38）和四氢可的松单葡糖醛酸盐（37、39）。