17-O-acetyl-3β-cyano-3α-O-(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)androst-4-ene-17β-ol | 217650-83-4

• 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: 17-O-acetyl-3β-cyano-3α-O-(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)androst-4-ene-17β-ol
• CAS: 217650-83-4
• 化学式: C₃₆H₄₉NO₁₂
• 分子量: 687.785
• InChiKey: FKXNIJJKRVAMIG-UVZZPYFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.24
• 重原子数：
  49.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  173.75
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  17-O-acetyl-3β-cyano-3α-O-(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)androst-4-ene-17β-ol 在 氢氧化钾 、 硫酸 、 sodium 作用下， 以 甲醇 为溶剂， 反应 36.0h， 生成 3-amidoandrost-3,5-diene-17β-ol
  参考文献：
  名称：

  Cyanoglycosylation products of 17-O-acetyl-testosterone

  摘要：

  17-O-Acetyl testosterone, which has no susceptible hydroxyl or carboxyl group for glycosylation, was glycosylated with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide in the presence of a mixed catalyst, Hg(CN)(2) and HgBr2, in benzene-nitromethane. Reaction occurred on the alpha, beta-unsaturated ketone on the six-membered A-ring to give six 3-O-glycosides, each bearing a cyano group at the 3- or 5-position of the aglycon, and a 3-O-glycoside bearing a CONH2 group at the 3-position. Structural analyses of these products were carried out by various NMR (H-1, C-13 NMR,H-1-H-1 and H-1-C-13 COSY, HMBC; and DEFT), FARMS and X-ray analyses. The mechanisms of the formations of the products are discussed. It was determined that mercuric cyanide was essential as a catalyst for the progress of the cyanoglycosylation. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00192-x
• 作为产物：
  描述：

  醋酸睾酮 、 氰化汞 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 mercury dibromide 作用下， 以 硝基甲烷 、 苯 为溶剂， 反应 16.0h， 以7.5%的产率得到Acetic acid (5S,8R,9S,10R,13S,14S,17S)-5-cyano-10,13-dimethyl-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-2,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester
  参考文献：
  名称：

  Cyanoglycosylation products of 17-O-acetyl-testosterone

  摘要：

  17-O-Acetyl testosterone, which has no susceptible hydroxyl or carboxyl group for glycosylation, was glycosylated with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide in the presence of a mixed catalyst, Hg(CN)(2) and HgBr2, in benzene-nitromethane. Reaction occurred on the alpha, beta-unsaturated ketone on the six-membered A-ring to give six 3-O-glycosides, each bearing a cyano group at the 3- or 5-position of the aglycon, and a 3-O-glycoside bearing a CONH2 group at the 3-position. Structural analyses of these products were carried out by various NMR (H-1, C-13 NMR,H-1-H-1 and H-1-C-13 COSY, HMBC; and DEFT), FARMS and X-ray analyses. The mechanisms of the formations of the products are discussed. It was determined that mercuric cyanide was essential as a catalyst for the progress of the cyanoglycosylation. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00192-x