(4S,5R)-5-(tert-butyldimethylsilanyloxy)-4-[(R)-1-(tert-butyldimethylsilanyloxy)allyl]oct-7-ynnitrile | 288380-99-4

• 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: (4S,5R)-5-(tert-butyldimethylsilanyloxy)-4-[(R)-1-(tert-butyldimethylsilanyloxy)allyl]oct-7-ynnitrile
• 英文别名: (4S,5R)-5-[tert-butyl(dimethyl)silyl]oxy-4-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyprop-2-enyl]oct-7-ynenitrile
• CAS: 288380-99-4
• 化学式: C₂₃H₄₃NO₂Si₂
• 分子量: 421.771
• InChiKey: LEFLSSYKNJDPOX-NJDAHSKKSA-N

物化性质

• 沸点：
  445.8±45.0 °C(Predicted)
• 密度：
  0.905±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S,5R)-5-(tert-butyldimethylsilanyloxy)-4-[(R)-1-(tert-butyldimethylsilanyloxy)allyl]oct-7-ynnitrile 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 二异丁基氢化铝 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 二甲基亚砜 、 甲苯 为溶剂， 反应 33.0h， 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
• 作为产物：
  描述：

  (3S,4R)-4-(tert-butyldimethylsilanyloxy)-3-[(R)-1-(tert-butyldimethylsilanyloxy)allyl]hept-6-ynnitrile 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 二异丁基氢化铝 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 、 甲苯 为溶剂， 反应 15.5h， 生成 (4S,5R)-5-(tert-butyldimethylsilanyloxy)-4-[(R)-1-(tert-butyldimethylsilanyloxy)allyl]oct-7-ynnitrile
  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

• Syntheses and biological evaluation of novel 2α-substituted 1α,25-dihydroxyvitamin D3 analogues
  作者：Yoshitomo Suhara、Ken-ichi Nihei、Hirokazu Tanigawa、Toshie Fujishima、Katsuhiro Konno、Kimie Nakagawa、Toshio Okano、Hiroaki Takayama

  DOI：10.1016/s0960-894x(00)00189-x

  日期：2000.5

  Novel 2 alpha-substituted 1 alpha,25-dihydroxyvitamin D-3 analogues were efficiently synthesized and their biological activities were evaluated. 2 alpha-Methyl-1 alpha,25-dihydroxyvitamin D-3 (2), whose unique biological activities were previously reported, was modified to 2 alpha-alkyl (ethyl and propyl) and 2 alpha-hydroxyalkyl (hydroxymethyl, hydroxyethyl, and hydroxypropyl) analogues 3-7 by elongation of the alkyl chain and/or introduction of a terminal hydroxyl group. 2 alpha-Hydroxypropyl-1 alpha,25-dihydroxyvitamin D-3 (7) exhibited an exceptionally potent calcium-regulating effect and a unique activity profile. (C) 2000 Elsevier Science Ltd. All rights reserved.