(20S)-20-(p-toluenesulfonyloxymethyl)pregna-1,5-dien-3α-ol | 177356-09-1

• 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: (20S)-20-(p-toluenesulfonyloxymethyl)pregna-1,5-dien-3α-ol
• 英文别名: [(2S)-2-[(3S,8S,9S,10R,13S,14S,17R)-3-hydroxy-10,13-dimethyl-4,7,8,9,11,12,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-17-yl]propyl] 4-methylbenzenesulfonate
• CAS: 177356-09-1
• 化学式: C₂₉H₄₀O₄S
• 分子量: 484.7
• InChiKey: NIWZPMMZMONRME-XVEOTDBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (20S)-20-(p-toluenesulfonyloxymethyl)pregna-1,5-dien-3α-ol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 对甲苯磺酸 、 sodium iodide 作用下， 以 氯仿 、 丙酮 、 甲苯 为溶剂， 反应 7.0h， 生成 (20S)-20-iodomethyl-2β-methoxy-pregn-5-en-1α,3α-diol
  参考文献：
  名称：

  Synthesis and biological activities of 26-hydroxy-27-nor-derivatives of 1α,25-dihydroxyvitamin D3

  摘要：

  Starting with (20S)-20-(p-toluenesulfonyl)oxymethyl-pregna-1,5-dien-3 alpha-ol (4), we synthesized three vitamin D analogs in 10 to 11 steps: 1 alpha,26-dihydroxy-27-nor-vitamin D-3 (1), its 3-epi analog (2), and 2 beta-methoxy-1 alpha,26-dihydroxy-27-nor-vitamin D-3 (3). We tested the derivatives in the murine mesenchymal cell line C3H10T1/2. All substances were less potent in inhibition of cell proliferation, inhibition of adipocyte differentiation, and induction of gene activation, and had a lower affinity to the vitamin D receptor than the native vitamin D-3 metabolite 1,25(OH)(2)D-3. The affinity of 1 to the vitamin D binding protein was about three limes higher than that of 1,25(OH)(2)D-3. (C) 1996 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(96)00120-1
• 作为产物：
  描述：

  (20S)-20-(p-Toluolsulfonyloxymethyl)pregna-1,5-dien-3-on 在 lithium tri-sec-butyl(hydrido)borate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以12%的产率得到(20S)-20-(p-toluenesulfonyloxymethyl)pregna-1,5-dien-3β-ol
  参考文献：
  名称：

  Umwandlung von (20S)-20-(Hydroxymethyl)pregna-1,4-dien-3-on in (20S)-20-(p-Toluolsulfonyloxymethyl)pregna-1,5-dien-3?-ol und -3?-ol: Zwischenprodukte f�r Vitamin D-Derivate

  摘要：

  Efficient three-step approaches to the two 3-epimeric 22-tosylated 1,5-diene-3,22-diols 6 and 7 starting with (20S)-20-(hydroxymethyl)pregna-1,4-dien-3-one (1) were developed and optimized. Isomerization of 1 to the 1,5-dien-3-one 3 and subsequent tosylation furnished the deconjugated 3-ketone 4. The 3 beta-alcohol 6 was available from 4 by means of in situ generated calcium borohydride. Treatment of 4 with lithium trisiamylborohydride (LS-Selectride) afforded the highest yield of the hitherto unknown 3 alpha-epimer 7. Following the optimized synthesis, 6 and 7 were obtained from 1 in 60% and 50% overall yield, respectively.

  DOI：

  10.1002/prac.19963380145

文献信息

• CYCLIC ETHER VITAMIN D3 COMPOUNDS, 1ALPHA (OH) 3-EPI-VITAMIN D3 COMPOUNDS AND USES THEREOF
  申请人：Woman & Infants Hospital

  公开号：EP0981523B1

  公开（公告）日：2005-12-07
• Umwandlung von (20S)-20-(Hydroxymethyl)pregna-1,4-dien-3-on in (20S)-20-(p-Toluolsulfonyloxymethyl)pregna-1,5-dien-3?-ol und -3?-ol: Zwischenprodukte f�r Vitamin D-Derivate
  作者：S. Wittmann、R. Krieg、R. Prousa、B. Sch�necker、P. Droescher

  DOI：10.1002/prac.19963380145

  日期：——

  Efficient three-step approaches to the two 3-epimeric 22-tosylated 1,5-diene-3,22-diols 6 and 7 starting with (20S)-20-(hydroxymethyl)pregna-1,4-dien-3-one (1) were developed and optimized. Isomerization of 1 to the 1,5-dien-3-one 3 and subsequent tosylation furnished the deconjugated 3-ketone 4. The 3 beta-alcohol 6 was available from 4 by means of in situ generated calcium borohydride. Treatment of 4 with lithium trisiamylborohydride (LS-Selectride) afforded the highest yield of the hitherto unknown 3 alpha-epimer 7. Following the optimized synthesis, 6 and 7 were obtained from 1 in 60% and 50% overall yield, respectively.
• Synthesis and biological activities of 26-hydroxy-27-nor-derivatives of 1α,25-dihydroxyvitamin D3
  作者：Dietmar Scheddin、Hubert Mayer、Steffen Wittmann、Bruno Schönecker、Sabine Gliesing、Manfred Reichenbächer

  DOI：10.1016/s0039-128x(96)00120-1

  日期：1996.10

  Starting with (20S)-20-(p-toluenesulfonyl)oxymethyl-pregna-1,5-dien-3 alpha-ol (4), we synthesized three vitamin D analogs in 10 to 11 steps: 1 alpha,26-dihydroxy-27-nor-vitamin D-3 (1), its 3-epi analog (2), and 2 beta-methoxy-1 alpha,26-dihydroxy-27-nor-vitamin D-3 (3). We tested the derivatives in the murine mesenchymal cell line C3H10T1/2. All substances were less potent in inhibition of cell proliferation, inhibition of adipocyte differentiation, and induction of gene activation, and had a lower affinity to the vitamin D receptor than the native vitamin D-3 metabolite 1,25(OH)(2)D-3. The affinity of 1 to the vitamin D binding protein was about three limes higher than that of 1,25(OH)(2)D-3. (C) 1996 by Elsevier Science Inc.