methyl 6-O-benzyl-2-O-tert-butyldimethylsilyl-3-deoxy-3-C-(3-pivaloyloxypropyl)-α-D-altropyranoside | 1030027-93-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-O-benzyl-2-O-tert-butyldimethylsilyl-3-deoxy-3-C-(3-pivaloyloxypropyl)-α-D-altropyranoside
• CAS: 1030027-93-0
• 化学式: C₂₈H₄₈O₇Si
• 分子量: 524.77
• InChiKey: HPKQFKBIVSPSRC-VAFBSOEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.31
• 重原子数：
  36.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  83.45
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 6-O-benzyl-2-O-tert-butyldimethylsilyl-3-deoxy-3-C-(3-pivaloyloxypropyl)-α-D-altropyranoside 在 N-甲基吲哚酮 、 四丙基高钌酸铵 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以86%的产率得到3-[(2R,4S,5S,6S)-2-benzyloxymethyl-5-(tert-butyldimethylsilyloxy)-6-methoxy-3-oxotetrahydropyran-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
• 作为产物：
  描述：

  methyl 4,6-O-benzylidene-2-(tert-butyldimethylsilyloxy)-3-deoxy-3-[(3-pivaloyloxy)propyl]-α-D-altropyranoside 在 三乙基硅烷 、 3 A molecular sieve 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以59%的产率得到methyl 6-O-benzyl-2-O-tert-butyldimethylsilyl-3-deoxy-3-C-(3-pivaloyloxypropyl)-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