(4R,5S,6R)-6-[(t-butyldimethylsilyl)oxy]-5-[3-{(t-butyldimethylsilyl)oxy}propoxy]-1-(trimethylsilyl)oct-7-en-1-yn-4-ol | 299411-11-3

• 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: (4R,5S,6R)-6-[(t-butyldimethylsilyl)oxy]-5-[3-{(t-butyldimethylsilyl)oxy}propoxy]-1-(trimethylsilyl)oct-7-en-1-yn-4-ol
• 英文别名: (4R,5S,6R)-6-[tert-butyl(dimethyl)silyl]oxy-5-[3-[tert-butyl(dimethyl)silyl]oxypropoxy]-1-trimethylsilyloct-7-en-1-yn-4-ol
• CAS: 299411-11-3
• 化学式: C₂₆H₅₄O₄Si₃
• 分子量: 514.969
• InChiKey: POYUBXINFJEZKX-SMIHKQSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.99
• 重原子数：
  33
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,5S,6R)-6-[(t-butyldimethylsilyl)oxy]-5-[3-{(t-butyldimethylsilyl)oxy}propoxy]-1-(trimethylsilyl)oct-7-en-1-yn-4-ol 在 2,6-二甲基吡啶 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (3R,4S,5R)-3,5-bis(tert-butyldimethylsilyloxy)-4-[3-(tert-butyldimethylsilyloxy)propoxy]oct-1-en-7-yne
  参考文献：
  名称：

  A Concise and Efficient Route to 2α-(ω-Hydroxyalkoxy)-1α,25-dihydroxyvitamin D₃:  Remarkably High Affinity to Vitamin D Receptor¹

  摘要：

  [GRAPHICS]A convenient and potentially valuable synthetic approach to the novel 2 alpha-functionalized 1 alpha,25-dihydroxyvitamin D-3 [1 alpha,25(OH)(2)D-3] derivatives (1a-c), which are the C2-epimer of ED-71 and its analogues, has been developed. The C2 alpha-modified ring A precursors (1,7-enynes 16, n = 0, 1, and 2) were constructed stereoselectively starting from D-glucose in high yield. In the synthesized 2 alpha-(omega-hydroxyalkoxy)-1 alpha,25(OH)(2)D-3 derivatives, la and Ib showed a greater binding affinity to vitamin D receptor (VDR), up to 1.8 times that of the native hormone.

  DOI：

  10.1021/ol006222j
• 作为产物：
  描述：

  methyl 4,6-O-benzylidene-3-O-[3-{(tert-butyldimethylsilyl)oxy}propyl]-α-D-altropyranoside 在 咪唑 、 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 三氟化硼乙醚 、 四丁基氟化铵 、 sodium methylate 、 sodium cyanoborohydride 、 barium carbonate 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 丙醇 、 四氯化碳 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.42h， 生成 (4R,5S,6R)-6-[(t-butyldimethylsilyl)oxy]-5-[3-{(t-butyldimethylsilyl)oxy}propoxy]-1-(trimethylsilyl)oct-7-en-1-yn-4-ol
  参考文献：
  名称：

  A Concise and Efficient Route to 2α-(ω-Hydroxyalkoxy)-1α,25-dihydroxyvitamin D₃:  Remarkably High Affinity to Vitamin D Receptor¹

  摘要：

  [GRAPHICS]A convenient and potentially valuable synthetic approach to the novel 2 alpha-functionalized 1 alpha,25-dihydroxyvitamin D-3 [1 alpha,25(OH)(2)D-3] derivatives (1a-c), which are the C2-epimer of ED-71 and its analogues, has been developed. The C2 alpha-modified ring A precursors (1,7-enynes 16, n = 0, 1, and 2) were constructed stereoselectively starting from D-glucose in high yield. In the synthesized 2 alpha-(omega-hydroxyalkoxy)-1 alpha,25(OH)(2)D-3 derivatives, la and Ib showed a greater binding affinity to vitamin D receptor (VDR), up to 1.8 times that of the native hormone.

  DOI：

  10.1021/ol006222j

文献信息

• Vitamin d derivatives having substituents at the 2 alpha-position
  申请人：——

  公开号：US20030022872A1

  公开（公告）日：2003-01-30

  An object of the present invention is to synthesize a novel vitamin D derivative having a substituent at the 2&agr;-position. According to the present invention, there is provided a vitamin D derivative of Formula (1): 1 wherein R 1 and R 2 are straight chained or branched lower alkyl which may be substituted with hydroxy.

  本发明的目的是合成一种在2α位置具有取代基的新型维生素D衍生物。根据本发明，提供了一种式(1)的维生素D衍生物：1 其中R1和R2是直链或支链的低级烷基，可以用羟基取代。
• A Concise and Efficient Route to 2α-(ω-Hydroxyalkoxy)-1α,25-dihydroxyvitamin D₃:  Remarkably High Affinity to Vitamin D Receptor¹
  作者：Atsushi Kittaka、Yoshitomo Suhara、Hitoshi Takayanagi、Toshie Fujishima、Masaaki Kurihara、Hiroaki Takayama

  DOI：10.1021/ol006222j

  日期：2000.8.1

  [GRAPHICS]A convenient and potentially valuable synthetic approach to the novel 2 alpha-functionalized 1 alpha,25-dihydroxyvitamin D-3 [1 alpha,25(OH)(2)D-3] derivatives (1a-c), which are the C2-epimer of ED-71 and its analogues, has been developed. The C2 alpha-modified ring A precursors (1,7-enynes 16, n = 0, 1, and 2) were constructed stereoselectively starting from D-glucose in high yield. In the synthesized 2 alpha-(omega-hydroxyalkoxy)-1 alpha,25(OH)(2)D-3 derivatives, la and Ib showed a greater binding affinity to vitamin D receptor (VDR), up to 1.8 times that of the native hormone.