(3R,4S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-4-butylnon-1-en-7-yne | 393165-47-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (3R,4S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-4-butylnon-1-en-7-yne
• 英文别名: tert-butyl-[(3R,4S,5R)-4-butyl-5-[tert-butyl(dimethyl)silyl]oxyoct-1-en-7-yn-3-yl]oxy-dimethylsilane
• CAS: 393165-47-4
• 化学式: C₂₄H₄₈O₂Si₂
• 分子量: 424.815
• InChiKey: AFSYTPFURYPDBR-YPAWHYETSA-N

物化性质

• 沸点：
  419.7±45.0 °C(Predicted)
• 密度：
  0.868±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.78
• 重原子数：
  28
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R,4S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-4-butylnon-1-en-7-yne 在 四(三苯基膦)钯 、 TEA 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 (1R,2S,3S)-2-Butyl-5-[2-[(1R,3aS,7aR)-1-((S)-5-hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-methylene-cyclohexane-1,3-diol
  参考文献：
  名称：

  Concise synthesis and biological activities of 2α-Alkyl- and 2α-(ω-Hydroxyalkyl)-20-epi-1α,25-dihydroxyvitamin D3

  摘要：

  We found a concise route to the Trost A-ring precursor enyne for synthesizing 2alpha-alkylated 1alpha,25-dihydroxyvitamin D-3 (1) from D-glucose. The enynes were coupled with the 20-epi-CD ring part to study the effect of the double modification of 2alpha-substitution and 20-epimerization upon biological activities of 1. The novel three analogues of 2alpha-alkyl- and four analogues of 2alpha-(omega-hydroxyalkyl)-20-epi-1alpha,25-dihydroxyvitamin D-3 (5b-d and 6a-d) showed higher binding affinity for vitamin D receptor (VDR) and more potent activity in induction of HL-60 cell differentiation than those of the natural hormone 1. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00739-x
• 作为产物：
  描述：

  benzyl 3-deoxy-3-C-methylene-2-O-methoxymethyl-5-O-pivaloyl-α-D-lyxo-pentofuranoside 在 20percent Pd(OH)2/C 咪唑 、 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 正丁基锂 、 三氟化硼乙醚 、 四丁基氟化铵 、 氢气 、 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 、 9-硼双环[3.3.1]壬烷 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 甲苯 、 叔丁醇 为溶剂， 反应 104.18h， 生成 (3R,4S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-4-butylnon-1-en-7-yne
  参考文献：
  名称：

  Efficient and Versatile Synthesis of Novel 2α-Substituted 1α,25-Dihydroxyvitamin D₃ Analogues and Their Docking to Vitamin D Receptors

  摘要：

  Novel 2 alpha -substituted 1 alpha ,25-dihydroxyvitamin D-3 analogues with 2 alpha -alkyl and 2 alpha -hydroxyalkyl groups were systematically synthesized from D-xylose. Their conformation on binding to the ligand binding domain (LBD) of the vitamin D receptor was analyzed. It has been found that the 2 alpha -hydroxypropyl group best fits the cavity of the LBD, and the binding activity is three times higher than that for the natural hormone.

  DOI：

  10.1021/jo010375i

文献信息

• Synthesis of 2α- and 2β-substituted-14-epi-previtamin D3 and their genomic activity
  作者：Daisuke Sawada、Tomoyuki Katayama、Yuya Tsukuda、Nozomi Saito、Hiroshi Saito、Ken-ichiro Takagi、Eiji Ochiai、Seiichi Ishizuka、Kazuya Takenouchi、Atsushi Kittaka

  DOI：10.1016/j.tet.2010.05.028

  日期：2010.7

  and 2β-Substituted analogs of 14-epi-previtamin D3 were synthesized and isolated after thermal isomerization of 14-epi-vitamin D3 triene at 80 °C. The VDR binding affinity and transactivation activity of osteocalcin promoter in HOS cells were tested, and the 2α-methyl-substituted analog was found to have greater genomic activity than 14-epi-previtamin D3. We found that modification at the C2 position

  14-表位-维生素D 3三烯在80°C下热异构化后，合成并分离了14-表位-维生素D 3的2α和2β取代类似物。在HOS细胞骨钙蛋白启动子的VDR结合亲和力和反式激活活性进行了测试，并且2α甲基取代的类似物被发现具有更大的基因组活性比14-外延-previtamin d 3。我们发现，在修改的C2位置塞科-steroidal骨架提供了对前维生素d形式的生物基因组活动以及天然维生素d形式有趣的效果。
• Synthesis of 2α-substituted-14-epi-previtamin D3 and its genomic activity
  作者：Daisuke Sawada、Tomoyuki Katayama、Yuya Tsukuda、Nozomi Saito、Masashi Takano、Hiroshi Saito、Ken-ichiro Takagi、Eiji Ochiai、Seiichi Ishizuka、Kazuya Takenouchi、Atsushi Kittaka

  DOI：10.1016/j.bmcl.2009.07.112

  日期：2009.9

  We synthesized and isolated 2 alpha-substituted analogs of 14-epi-previtamin D-3 after thermal isomerization at 80 degrees C for the first time. The VDR binding affinity and transactivation activity of osteocalcin promoter in HOS cells were evaluated, and the 2 alpha-methyl-substituted analog was found to have greater genomic activity than 14-epi-previtamin D-3. (C) 2009 Elsevier Ltd. All rights reserved.