methyl 4,6-O-benzylidene-2-O-(tert-butyldimethylsilyl)-3-C-{3-(tert-butyldiphenylsilyloxy)propyl}-3-deoxy-α-D-altopyranoside | 1030028-14-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: methyl 4,6-O-benzylidene-2-O-(tert-butyldimethylsilyl)-3-C-{3-(tert-butyldiphenylsilyloxy)propyl}-3-deoxy-α-D-altopyranoside
• CAS: 1030028-14-8
• 化学式: C₃₉H₅₆O₆Si₂
• 分子量: 677.041
• InChiKey: PHAQBKZWMLAQPK-MQAQGHKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.84
• 重原子数：
  47.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 4,6-O-benzylidene-2-O-(tert-butyldimethylsilyl)-3-C-{3-(tert-butyldiphenylsilyloxy)propyl}-3-deoxy-α-D-altopyranoside 在 lithium 作用下， 以 四氢呋喃 、 氨 为溶剂， 反应 0.25h， 以95%的产率得到methyl 2-O-(tert-butyldimethylsilyl)-3-C-{3-(tert-butyldiphenylsilyloxy)propyl}-3-deoxy-α-D-altopyranoside
  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 4,6-O-benzylidene-3-C-{3-(tert-butyldiphenylsilyloxy)propyl}-3-deoxy-α-D-altopyranoside 、 叔丁基二甲硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以96%的产率得到methyl 4,6-O-benzylidene-2-O-(tert-butyldimethylsilyl)-3-C-{3-(tert-butyldiphenylsilyloxy)propyl}-3-deoxy-α-D-altopyranoside
  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