3-[(2S,3S,4R,5S,6S)-2-bromomethyl-5-(tert-butyldimethylsilyloxy)-6-methoxy-3-pivaloyloxymethyltetrahydropyran-4-yl]propyl pivalate | 1030028-01-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[(2S,3S,4R,5S,6S)-2-bromomethyl-5-(tert-butyldimethylsilyloxy)-6-methoxy-3-pivaloyloxymethyltetrahydropyran-4-yl]propyl pivalate
• CAS: 1030028-01-3
• 化学式: C₂₇H₅₁BrO₇Si
• 分子量: 595.687
• InChiKey: BAETVAFKTJXBHN-YXIAPDDASA-N

反应信息

• 作为反应物：
  描述：

  3-[(2S,3S,4R,5S,6S)-2-bromomethyl-5-(tert-butyldimethylsilyloxy)-6-methoxy-3-pivaloyloxymethyltetrahydropyran-4-yl]propyl pivalate 在 sodium cyanoborohydride 、 锌 作用下， 以 丙醇 、 水 为溶剂， 反应 4.0h， 以88%的产率得到(4R,5S)-4-[(S)-1-(tert-butyldimethylsilyloxy)-2-hydroxyethyl]-5-(pivaloyloxymethyl)-hept-6-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：

  3-[(2S,3S,4R,5S,6S)-5-(tert-butyldimethylsilyloxy)-2-methanesulfonyloxymethyl-6-methoxy-3-pivaloyloxymethyltetrahydropyran-4-yl]propyl pivalate 在 lithium bromide 作用下， 以 various solvent(s) 为溶剂， 反应 6.5h， 以91%的产率得到3-[(2S,3S,4R,5S,6S)-2-bromomethyl-5-(tert-butyldimethylsilyloxy)-6-methoxy-3-pivaloyloxymethyltetrahydropyran-4-yl]propyl 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