3β-[(t-butyldimethylsilyl)oxy]-20(S)-(cyanomethyl)-9,10-secopregna-5(E),7(E),10(19)-triene | 167892-92-4

• 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: 3β-[(t-butyldimethylsilyl)oxy]-20(S)-(cyanomethyl)-9,10-secopregna-5(E),7(E),10(19)-triene
• CAS: 167892-92-4
• 化学式: C₂₉H₄₇NOSi
• 分子量: 453.784
• InChiKey: BWGGFCSXUYLRMV-AXQGLMQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.74
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  33.02
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3β-[(t-butyldimethylsilyl)oxy]-20(S)-(cyanomethyl)-9,10-secopregna-5(E),7(E),10(19)-triene 在 吡啶 、 咪唑 、 氢氧化钾 、 sodium tetrahydroborate 、 selenium(IV) oxide 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 蒽 、 四丁基氟化铵 、 二异丁基氢化铝 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 8.26h， 生成 23(S),25-epoxy-26,26,26,27,27,27-hexafluoro-9,10-secocholesta-5(Z),7(E),10(19)-triene
  参考文献：
  名称：

  Synthesis and biological evaluations of C-23-modified 26,26,26,27,27,27-F 6 -vitamin D 3 analogues

  摘要：

  A convenient synthetic method which could allow flexible modification at C-23 of 26,26,26,27,27,27-hexafluoro-1 alpha,25-dihydroxyvitamin D-3 (3) has been developed. An effective construction of hexafluoroacetone (HFA) aldol part on the side chain of 10 was achieved by aldol reaction with HFA gas. This route is also attractive as an approach to diverse 26,27-modified vitamin D3 analogues. The preliminary biological activities of 23-modifed 26,27-F-6 vitamin D3 analogues are evaluated. The potency of VDR affinities of the C-23-substituted analogues (keto group (4); OH group (5a,5b); fluorine atom (6a,6b); and oxetane ring (7a,7b)) was found to vary depending upon both the nature and stereochemistry of the substituents. In contrast, the HL-60 cell differentiation property was less varied than VDR affinity, and depended upon the nature rather than the stereochemistry of the substituents. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00106-1
• 作为产物：
  描述：

  氰化钾 、 (5E,7E,20S)-3β-(tert-butyldimethylsilyloxy)-20-(p-tolylsulfonyloxymethyl)-9,10-seco-5,7,10(19)-pregnatriene 以 二甲基亚砜 为溶剂， 反应 0.5h， 以70%的产率得到3β-[(t-butyldimethylsilyl)oxy]-20(S)-(cyanomethyl)-9,10-secopregna-5(E),7(E),10(19)-triene
  参考文献：
  名称：

  Synthesis and biological evaluations of C-23-modified 26,26,26,27,27,27-F 6 -vitamin D 3 analogues

  摘要：

  A convenient synthetic method which could allow flexible modification at C-23 of 26,26,26,27,27,27-hexafluoro-1 alpha,25-dihydroxyvitamin D-3 (3) has been developed. An effective construction of hexafluoroacetone (HFA) aldol part on the side chain of 10 was achieved by aldol reaction with HFA gas. This route is also attractive as an approach to diverse 26,27-modified vitamin D3 analogues. The preliminary biological activities of 23-modifed 26,27-F-6 vitamin D3 analogues are evaluated. The potency of VDR affinities of the C-23-substituted analogues (keto group (4); OH group (5a,5b); fluorine atom (6a,6b); and oxetane ring (7a,7b)) was found to vary depending upon both the nature and stereochemistry of the substituents. In contrast, the HL-60 cell differentiation property was less varied than VDR affinity, and depended upon the nature rather than the stereochemistry of the substituents. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00106-1