methyl 6-bromo-2-O-(tert-butyldimethylsilyl)-3-C-{3-(tert-butyldiphenylsilyloxy)propyl}-3,4,6-trideoxy-α-D-altropyranoside | 1030028-23-9

• 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: methyl 6-bromo-2-O-(tert-butyldimethylsilyl)-3-C-{3-(tert-butyldiphenylsilyloxy)propyl}-3,4,6-trideoxy-α-D-altropyranoside
• CAS: 1030028-23-9
• 化学式: C₃₂H₅₁BrO₄Si₂
• 分子量: 635.83
• InChiKey: IBUOHCHRLLWCSS-UUHGVMMKSA-N

物化性质

• 沸点：
  578.2±50.0 °C(predicted)
• 密度：
  1.12±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.51
• 重原子数：
  39.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 6-bromo-2-O-(tert-butyldimethylsilyl)-3-C-{3-(tert-butyldiphenylsilyloxy)propyl}-3,4,6-trideoxy-α-D-altropyranoside 在 水 、 sodium cyanoborohydride 、 锌 作用下， 以 丙醇 为溶剂， 反应 0.67h， 以81%的产率得到(2S,3R)-2-(tert-butyldimethylsilyloxy)-3-(tert-butyldiphenylsilyloxy)hex-5-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：

  methyl 2-O-(tert-butyldimethylsilyl)-3-C-{3-(tert-butyldiphenylsilyloxy)propyl}-3,4-dideoxy-6-O-(methanesulfonyl)-α-D-altropyranoside 在 lithium bromide 作用下， 以 丁酮 为溶剂， 反应 7.0h， 以91%的产率得到methyl 6-bromo-2-O-(tert-butyldimethylsilyl)-3-C-{3-(tert-butyldiphenylsilyloxy)propyl}-3,4,6-trideoxy-α-D-altropyranoside
  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