methyl 6-bromo-2,4-bis-(O-tert-butyldimethylsilyl)-3-O-[3-{(tert-butyldimethylsilyl)oxy}propyl]-6-deoxy-α-D-altropyranoside | 299411-01-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-bromo-2,4-bis-(O-tert-butyldimethylsilyl)-3-O-[3-{(tert-butyldimethylsilyl)oxy}propyl]-6-deoxy-α-D-altropyranoside
• 英文别名: Methyl 6-bromo-2,4-bis-(O-t-butyldimethylsilyl)-3-O-[3-{(t-butyldimethylsilyl)oxy}propyl]-6-deoxy-α-D-altropyranoside；3-[(2S,3S,4R,5S,6S)-2-(bromomethyl)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-6-methoxyoxan-4-yl]oxypropoxy-tert-butyl-dimethylsilane
• CAS: 299411-01-1
• 化学式: C₂₈H₆₁BrO₆Si₃
• 分子量: 657.949
• InChiKey: KOWXBEVYLIONEP-LFCBLZOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.33
• 重原子数：
  38
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 6-bromo-2,4-bis-(O-tert-butyldimethylsilyl)-3-O-[3-{(tert-butyldimethylsilyl)oxy}propyl]-6-deoxy-α-D-altropyranoside 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 正丁基锂 、 三氟化硼乙醚 、 四丁基氟化铵 、 sodium cyanoborohydride 、 potassium carbonate 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 丙醇 、 二氯甲烷 、 水 为溶剂， 反应 0.75h， 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 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside 在 咪唑 、 N-溴代丁二酰亚胺(NBS) 、 potassium tert-butylate 、 sodium methylate 、 barium carbonate 作用下， 以 甲醇 、 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.67h， 生成 methyl 6-bromo-2,4-bis-(O-tert-butyldimethylsilyl)-3-O-[3-{(tert-butyldimethylsilyl)oxy}propyl]-6-deoxy-α-D-altropyranoside
  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.