4-{(1S)-1-(tert-butyldimethylsilyloxy)-2-(p-toluenesulfonyloxy)}ethyl-7-(tert-butyldiphenylsilyloxy)hept-1-ene | 1030028-25-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-{(1S)-1-(tert-butyldimethylsilyloxy)-2-(p-toluenesulfonyloxy)}ethyl-7-(tert-butyldiphenylsilyloxy)hept-1-ene
• CAS: 1030028-25-1
• 化学式: C₃₈H₅₆O₅SSi₂
• 分子量: 681.097
• InChiKey: SCBYJOBZADEDJS-LBHUVFDKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.64
• 重原子数：
  46.0
• 可旋转键数：
  16.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-{(1S)-1-(tert-butyldimethylsilyloxy)-2-(p-toluenesulfonyloxy)}ethyl-7-(tert-butyldiphenylsilyloxy)hept-1-ene 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以75%的产率得到(4R)-4-[(S)-oxiranyl]hept-6-en-1-ol
  参考文献：
  名称：

  The 2α-(3-hydroxypropyl) group as an active motif in vitamin D3 analogues as agonists of the mutant vitamin D receptor (Arg274Leu)

  摘要：

  We designed and synthesized 1 alpha- and 1 beta-hydroxymethyl-2 alpha-(3-hydroxypropyl)-25-hydroxyvitamin D-3 (2a,b) and related analogues 2 alpha-(3-hydroxypropyl)-25-hydroxyvitamin D-3 (3), Posner's analogues of 1 alpha- and 1 beta-hydroxymethyl-25-hydroxyvitamin D-3 (4a,b), as well as 2 alpha-(3-hydroxypropyl)-1 alpha,25-dihydroxyvitamin D-3 (5), to confirm the effect of the 1 alpha-hydroxy group and/or 2 alpha-(3-hydroxypropyl) group of vitamin D-3 analogues with the modified A-ring moiety on the mutant vitamin D receptor, VDR(Arg274Leu). The 2 alpha-(3-hydroxypropyl) group showed better effect on enhancement of the transcriptional activity through the mutant VDR than the 1 alpha- and 1 beta-hydroxymethyl groups. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.12.039
• 作为产物：
  描述：

  (2S,3R)-2-(tert-butyldimethylsilyloxy)-3-(tert-butyldiphenylsilyloxy)hex-5-en-1-ol 、 对甲苯磺酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以91%的产率得到4-{(1S)-1-(tert-butyldimethylsilyloxy)-2-(p-toluenesulfonyloxy)}ethyl-7-(tert-butyldiphenylsilyloxy)hept-1-ene
  参考文献：
  名称：

  The 2α-(3-hydroxypropyl) group as an active motif in vitamin D3 analogues as agonists of the mutant vitamin D receptor (Arg274Leu)

  摘要：

  We designed and synthesized 1 alpha- and 1 beta-hydroxymethyl-2 alpha-(3-hydroxypropyl)-25-hydroxyvitamin D-3 (2a,b) and related analogues 2 alpha-(3-hydroxypropyl)-25-hydroxyvitamin D-3 (3), Posner's analogues of 1 alpha- and 1 beta-hydroxymethyl-25-hydroxyvitamin D-3 (4a,b), as well as 2 alpha-(3-hydroxypropyl)-1 alpha,25-dihydroxyvitamin D-3 (5), to confirm the effect of the 1 alpha-hydroxy group and/or 2 alpha-(3-hydroxypropyl) group of vitamin D-3 analogues with the modified A-ring moiety on the mutant vitamin D receptor, VDR(Arg274Leu). The 2 alpha-(3-hydroxypropyl) group showed better effect on enhancement of the transcriptional activity through the mutant VDR than the 1 alpha- and 1 beta-hydroxymethyl groups. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.12.039