(2S,3S,5S,6S)-2-bromomethyl-5-(tert-butyldimethylsilyloxy)-6-methoxytetrahydropyran-3-ylmethyl pivalate | 1030028-35-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,5S,6S)-2-bromomethyl-5-(tert-butyldimethylsilyloxy)-6-methoxytetrahydropyran-3-ylmethyl pivalate
• CAS: 1030028-35-3
• 化学式: C₁₉H₃₇BrO₅Si
• 分子量: 453.489
• InChiKey: TUDVRQWUISPOQB-JONQDZQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.74
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,5S,6S)-2-bromomethyl-5-(tert-butyldimethylsilyloxy)-6-methoxytetrahydropyran-3-ylmethyl pivalate 在 sodium cyanoborohydride 、 锌 作用下， 以 丙醇 、 水 为溶剂， 反应 12.0h， 以75%的产率得到(R)-2-[(S)-2-(tert-butyldimethylsilyloxy)-3-hydroxyiropyl]but-3-enyl pivalate
  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：

  在 lithium bromide 作用下， 以 various solvent(s) 为溶剂， 反应 7.0h， 以476.4 mg的产率得到(2S,3S,5S,6S)-2-bromomethyl-5-(tert-butyldimethylsilyloxy)-6-methoxytetrahydropyran-3-ylmethyl pivalate
  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