(3R,4S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-4-[2-(tert-butyldimethylsilanyloxy)ethyl]oct-1-en-7-yne | 288380-85-8

• 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-[2-(tert-butyldimethylsilanyloxy)ethyl]oct-1-en-7-yne
• 英文别名: tert-butyl-[(3R,4S,5R)-5-[tert-butyl(dimethyl)silyl]oxy-4-[2-[tert-butyl(dimethyl)silyl]oxyethyl]oct-1-en-7-yn-3-yl]oxy-dimethylsilane
• CAS: 288380-85-8
• 化学式: C₂₈H₅₈O₃Si₃
• 分子量: 527.023
• InChiKey: PFGZSGBEFRCUSM-UBFVSLLYSA-N

物化性质

• 沸点：
  477.6±45.0 °C(Predicted)
• 密度：
  0.882±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.0
• 重原子数：
  34
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-4-[2-(tert-butyldimethylsilanyloxy)ethyl]oct-1-en-7-yne 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 TEA 、 camphor-10-sulfonic acid 、 焦磷酸硫胺素 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 (1R,2S,3S,5Z)-5-[(2E)-2-[(3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-2-(2-hydroxyethyl)-4-methylidenecyclohexane-1,3-diol
  参考文献：
  名称：

  Syntheses and biological evaluation of novel 2α-substituted 1α,25-dihydroxyvitamin D3 analogues

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(00)00189-x
• 作为产物：
  描述：

  1,2-O-isopropylidene-5-O-2,2-dimethylpropanoyl-α-D-erythro-pent-3-ulofuranose 在 palladium dihydroxide 吡啶 、 咪唑 、 2,6-二甲基吡啶 、 盐酸 、 甲醇 、 4-二甲氨基吡啶 、 sodium hydroxide 、 sodium tetrahydroborate 、 9-borabicyclo[3.3.1]nonane dimer 、 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 、 四丁基碘化铵 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 、 三苯基膦 、 lithium hexamethyldisilazane 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 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， 生成 (3R,4S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-4-[2-(tert-butyldimethylsilanyloxy)ethyl]oct-1-en-7-yne
  参考文献：
  名称：

  Syntheses and biological evaluation of novel 2α-substituted 1α,25-dihydroxyvitamin D3 analogues

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(00)00189-x

文献信息

• Concise synthesis and biological activities of 2α-Alkyl- and 2α-(ω-Hydroxyalkyl)-20-epi-1α,25-dihydroxyvitamin D3
  作者：Shinobu Honzawa、Yoshitomo Suhara、Ken-ichi Nihei、Nozomi Saito、Seishi Kishimoto、Toshie Fujishima、Masaaki Kurihara、Takayuki Sugiura、Keizo Waku、Hiroaki Takayama、Atsushi Kittaka

  DOI：10.1016/s0960-894x(03)00739-x

  日期：2003.10

  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.
• Efficient and Versatile Synthesis of Novel 2α-Substituted 1α,25-Dihydroxyvitamin D₃ Analogues and Their Docking to Vitamin D Receptors
  作者：Yoshitomo Suhara、Ken-ichi Nihei、Masaaki Kurihara、Atsushi Kittaka、Kentaro Yamaguchi、Toshie Fujishima、Katsuhiro Konno、Naoki Miyata、Hiroaki Takayama

  DOI：10.1021/jo010375i

  日期：2001.12.1

  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.