1α,3β-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-23-oxo-9,10-secocholesta-5(Z),7(E),10(19)-trien-25-ol | 167893-00-7

• 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: 1α,3β-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-23-oxo-9,10-secocholesta-5(Z),7(E),10(19)-trien-25-ol
• 英文别名: (5Z,7E)-(1S,3R)-1,3-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-23-oxo-9,10-seco-5,7,10(19)-cholestatrien-25-ol
• CAS: 167893-00-7
• 化学式: C₃₉H₆₄F₆O₄Si₂
• 分子量: 767.096
• InChiKey: QYNYWTOETOXJMD-FLJXYBCHSA-N

物化性质

• 沸点：
  651.6±55.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.03
• 重原子数：
  51.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1α,3β-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-23-oxo-9,10-secocholesta-5(Z),7(E),10(19)-trien-25-ol 在 咪唑 、 氢氧化钾 、 sodium tetrahydroborate 、 甲烷磺酸 、 三正丁基氢锡 、 sodium hydride 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 氯仿 、 甲苯 为溶剂， 反应 19.17h， 生成 氟骨三醇
  参考文献：
  名称：

  Synthesis and biological evaluations of A-ring isomers of 26,26,26,27,27,27-hexafluoro-1,25-dihydroxyvitamin D 3

  摘要：

  The activated vitamin D-3 derivative 26,27-F-6-1 alpha,25(OH)(2)D-3 (2a), its three A-ring diastereomers (2b, 2c, 2d), and 5,6-trans isomer (2e) were prepared. Two analogues (2b, 2c) of these isomers were synthesized by a palladium catalyzed coupling reaction using Vinyl bromide 5 and enynes (6a, 6b), which were derived from readily commercially available 2S-(+)-glycidyl p-toluenesulfonate 7, as a common starting material. Competitive vitamin D receptor (VDR) binding affinities of these diastereomers of 2a were evaluated. Interestingly, the stereochemical effects at C-1,3 of 2a were considerably more moderate than those of 1 alpha,25(OH)(2)D-3 (1). In particular, isomerization at the 5,6-double bond of 2a only slightly reduced VDR affinity, whereas 5,6-trans-1 alpha,25(OH)(2)D-3 had a significantly lower binding affinity than 1. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00142-5
• 作为产物：
  描述：

  1α,3β-bis[(t-butyldimethylsilyl)oxy]-20(S)-(n-propyl-23-oxo)-9,10-secopregna-5(Z),7(E),10(19)-triene 以82的产率得到1α,3β-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-23-oxo-9,10-secocholesta-5(Z),7(E),10(19)-trien-25-ol
  参考文献：
  名称：

  Bioorg. Med. Chem. 2000, 8, 2157-2166

  摘要：

  DOI：

文献信息

• Synthesis and biological evaluations of C-23-modified 26,26,26,27,27,27-F 6 -vitamin D 3 analogues
  作者：Masahiko Ikeda、Haruki Matsumura、Nobuyuki Sawada、Katsuhiro Hashimoto、Tomoyuki Tanaka、Toshihiro Noguchi、Masaji Hayashi

  DOI：10.1016/s0968-0896(00)00106-1

  日期：2000.7

  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.