(8R,9S,10S,13S,14S)-10-[[tert-butyl(dimethyl)silyl]oxymethyl]-7,7-dideuterio-13-methyl-1,2,6,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,17-dione | 222557-27-9

• 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: (8R,9S,10S,13S,14S)-10-[[tert-butyl(dimethyl)silyl]oxymethyl]-7,7-dideuterio-13-methyl-1,2,6,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,17-dione
• CAS: 222557-27-9
• 化学式: C₂₅H₄₀O₃Si
• 分子量: 418.66
• InChiKey: VNYVXPVAMOILSK-ZIFJCERNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.09
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (8R,9S,10S,13S,14S)-10-[[tert-butyl(dimethyl)silyl]oxymethyl]-7,7-dideuterio-13-methyl-1,2,6,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,17-dione 在 sodium tetrahydroborate 、 三氯化铝 、 lithium aluminium deuteride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 6.5h， 生成 (8R,9S,10S,13S,14S,17S)-10-[[tert-butyl(dimethyl)silyl]oxymethyl]-3,3,7,7-tetradeuterio-13-methyl-2,6,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-ol
  参考文献：
  名称：

  Synthesis of Deuterium-Labeled Androst-5-ene-17.BETA.,19-diol and Its 4-Ene Isomer as Internal Standards for the Determination of the 19-Oxygenation of Aromatase Inhibitors Using GC-MS.

  摘要：

  [3β, 7, 7, 17α-2H4]Androst-5-ene-17β, 19-diol (6)和[3, 3, 7, 7, -2H4]androst-4-ene-17β, 19-diol (15-d4)被合成为气相色谱-质谱分析的内部标准，用于使用人胎盘芳香化酶对雄甾-5-烯-17-酮（1）及其4-烯异构体2（雌激素生物合成的抑制剂）的19-羟基化反应进行分析。用Zn-NaI-D2O处理[7, 7-2H2]3β-对甲苯磺酸酯3，然后用NaBD4

  DOI：

  10.1248/cpb.47.263
• 作为产物：
  描述：

  3β,17β-diacetoxy-19-(tert-butyldimethylsiloxy)androst-5-en-7-one 在 chromium(VI) oxide 、 三氯化铝 、 lithium aluminium deuteride 、 硫酸 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 丙酮 为溶剂， 反应 5.92h， 生成 (8R,9S,10S,13S,14S)-10-[[tert-butyl(dimethyl)silyl]oxymethyl]-7,7-dideuterio-13-methyl-1,2,6,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,17-dione
  参考文献：
  名称：

  Synthesis of Deuterium-Labeled Androst-5-ene-17.BETA.,19-diol and Its 4-Ene Isomer as Internal Standards for the Determination of the 19-Oxygenation of Aromatase Inhibitors Using GC-MS.

  摘要：

  [3β, 7, 7, 17α-2H4]Androst-5-ene-17β, 19-diol (6)和[3, 3, 7, 7, -2H4]androst-4-ene-17β, 19-diol (15-d4)被合成为气相色谱-质谱分析的内部标准，用于使用人胎盘芳香化酶对雄甾-5-烯-17-酮（1）及其4-烯异构体2（雌激素生物合成的抑制剂）的19-羟基化反应进行分析。用Zn-NaI-D2O处理[7, 7-2H2]3β-对甲苯磺酸酯3，然后用NaBD4

  DOI：

  10.1248/cpb.47.263

文献信息

• Synthesis of Deuterium-Labeled Androst-5-ene-17.BETA.,19-diol and Its 4-Ene Isomer as Internal Standards for the Determination of the 19-Oxygenation of Aromatase Inhibitors Using GC-MS.
  作者：Masao NAGAOKA、Makoto MORIO、Mitsuteru NUMAZAWA

  DOI：10.1248/cpb.47.263

  日期：——

  [3β, 7, 7, 17α-2H4]Androst-5-ene-17β, 19-diol (6) and [3, 3, 7, 7, -2H4]androst-4-ene-17β, 19-diol (15-d4) were synthesized as internal standards for gas chromatographic-mass spectrometric analysis of the 19-hydroxylation of androst-5-en-17-one (1) and its 4-ene isomer 2, inhibitors of estrogen biosynthesis, using human placental aromatase. Treatment of [7, 7-2H2]3β-tosylate 3 with Zn-NaI-D2O, followed by reduction with NaBD4, gave compound 6 (d4, 79.8 atom%). Compound 15-d4 was synthesized via 3β, 17β-dihydroxy-5-en-7-one 10 as a key intermediate. Deoxygenation of the 5-en-7-one 10 and [7, 7-2H2]17β-hydroxy-4-en-3-one 13-d2, produced from compound 10 in two steps, with AlCl2D2 was used for the deuterium labeling reaction, producing compound 15-d4 (d4, 93.5 atom%). The 19-oxygenation products of aromatase inhibitors 1 and 2 could be analyzed, after NaBH4 reduction, as the corresponding 17β, 19-diol bis-trimethylsilyl ethers using the internal standards 6 and 15-d4.

  [3β, 7, 7, 17α-2H4]Androst-5-ene-17β, 19-diol (6)和[3, 3, 7, 7, -2H4]androst-4-ene-17β, 19-diol (15-d4)被合成为气相色谱-质谱分析的内部标准，用于使用人胎盘芳香化酶对雄甾-5-烯-17-酮（1）及其4-烯异构体2（雌激素生物合成的抑制剂）的19-羟基化反应进行分析。用Zn-NaI-D2O处理[7, 7-2H2]3β-对甲苯磺酸酯3，然后用NaBD4