17b-hydroxy-14β-androst-5-en-3β-yl acetate | 133522-46-0

• 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: 17b-hydroxy-14β-androst-5-en-3β-yl acetate
• 英文别名: (3β,14β,17β)-androst-5-ene-3,17-diol 3-acetate；[(3S,8R,9S,10R,13S,14R,17S)-17-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 133522-46-0
• 化学式: C₂₁H₃₂O₃
• 分子量: 332.483
• InChiKey: OQHMNEGOKQMOFM-YQUGOWONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  17b-hydroxy-14β-androst-5-en-3β-yl acetate 生成 14β-androst-5-en-3β-yl acetate
  参考文献：
  名称：

  CERNY, IVAN;POUZAR, VLADIMIR;BUDESINSKY, MILOS;DRASAR, PAVEL;HAVEL, MIROS+, COLLECT. CZECHOSL. CHEM. COMMUN., 55,(1990) N0, C. 2510-2520

  摘要：

  DOI：
• 作为产物：
  描述：

  3β-hydroxy-14β-androst-5-en-17-one 在 吡啶 、 sodium tetrahydroborate 、 sodium nitrite 作用下， 以 甲醇 、 六甲基磷酰三胺 、 乙酸乙酯 为溶剂， 反应 5.08h， 生成 17b-hydroxy-14β-androst-5-en-3β-yl acetate
  参考文献：
  名称：

  Cerny, Ivan; Pouzar, Vladimir; Budesinsky, Milos, Collection of Czechoslovak Chemical Communications, 1990, vol. 55, # 10, p. 2510 - 2520

  摘要：

  DOI：

文献信息

• Glucosylation of Some Steroidal 17-Hydroxy Derivatives
  作者：Ivan Černý、Vladimír Pouzar、Pavel Drašar、Miroslav Havel

  DOI：10.1135/cccc19920362

  日期：——

  Eight 17-monoglucosides derived from androst-5-ene-3,17-diol, 14β-androst-5-ene-3,17-diol, 5β-androstane-3,17-diol and estradiol derivatives differing in configuration in the positions 17 and 3, have been prepared. The silver silicate - catalyzed glycosylation with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide gave 43-72% of the corresponding peracetylated β-D-glucopyranosides. The starting selectively protected 5β-androstane-3,17-diol derivatives were synthesized by a procedure utilizing orthogonality of the pivalate, acetate and nitrate protecting groups.

  从雄烯二醇-5-烯-3,17、14β-雄烯二醇-5-烯-3,17、5β-雄甾烷-3,17-二醇和雌二醇衍生物中，制备了八种单葡萄糖苷，它们在位置17和3的构型不同。使用2,3,4,6-四<斜体>O-乙酰基-α-D-葡萄糖吡喃糖溴化物和银硅酸盐催化的糖基化反应，得到了相应的过乙酰化β-D-葡萄糖吡喃糖的43-72%。起始的选择性保护的5β-雄甾烷-3,17-二醇衍生物是通过利用戊酸、乙酸和硝酸保护基的正交性而合成的。
• 14.BETA.,17-ALPHA-HYDROXYMETHYLANDROSTANE DERIVATIVES AS ANDROGENS
  申请人：Akzo Nobel N.V.

  公开号：EP1163259B1

  公开（公告）日：2002-11-20
• US6881728B1
  申请人：——

  公开号：US6881728B1

  公开（公告）日：2005-04-19
• [EN] 14.BETA., 17-ALPHA-HYDROXYMETHYLANDROSTANE DERIVATIVES AS ANDROGENS<br/>[FR] DERIVES DE 14.BETA., ALPHA-HYDROXYMETHYLANDROSTANE INTERVENANT COMME ANDROGENES
  申请人：AKZO NOBEL NV

  公开号：WO2000053619A1

  公开（公告）日：2000-09-14

  The disclosed invention relates to the unexpected finding of steroids for use as androgens which are characterized by a configuration opposite to that of natural steroids, viz. 14α, 17β. These steroids according to the invention are (14β, 17α)-17-(hydroxymethyl) steroids, and they are found to have in common an androgenic activity. They can be used for the preparation of an agent for male contraception, as well as for the preparation of a medicament for the treatment of androgen insufficiency.
• Cerny, Ivan; Pouzar, Vladimir; Budesinsky, Milos, Collection of Czechoslovak Chemical Communications, 1990, vol. 55, # 10, p. 2510 - 2520
  作者：Cerny, Ivan、Pouzar, Vladimir、Budesinsky, Milos、Drasar, Pavel、Havel, Miroslav

  DOI：——

  日期：——