(3R,4R,5R)-3,4,5-tris(triethylsilyloxy)-oct-1-en-7-yne | 930767-52-5

• 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: (3R,4R,5R)-3,4,5-tris(triethylsilyloxy)-oct-1-en-7-yne
• CAS: 930767-52-5
• 化学式: C₂₆H₅₄O₃Si₃
• 分子量: 498.969
• InChiKey: DAQGKHQPESHURH-CYXNTTPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.37
• 重原子数：
  32.0
• 可旋转键数：
  19.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3R,4R,5R)-3,4,5-tris(triethylsilyloxy)-oct-1-en-7-yne 、 (1R,3aR,7aR)-4-[(E)-bromomethylene]-1-[(1R,4R)-4,5-di(tert-butyldimethylsilyloxy)-1,5-dimethylhexyl]-7a-methyloctahydro-1H-indene 在 四(三苯基膦)钯 三乙胺 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以23%的产率得到1α,2β,3β-tris(triethylsilyloxy)-24R,25-di(tert-butyldimethylsilyloxy)-9,10-secocholesta-5,7,10(19)-triene
  参考文献：
  名称：

  Synthesis of putative metabolites of 1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3 (ED-71)

  摘要：

  1 alpha,25-Dihydroxy-2 beta-(3-hydroxypropoxy)vitamin D-3 (ED-71), an analog of active vitamin D-3, 1 alpha,25-dihydroxyvitamin D-3 [1,25(OH)(2)D-3] is under phase III clinical trials in Japan for the treatment of osteoporosis and bone fracture prevention. Since ED-71 has a substituent at the 2 beta-position of the A-ring, it is recognized that the metabolic pathway of ED-71 might be more complicated than 1,25(OH)(2)D-3 because of metabolism at the 2 beta-position substituent in addition to the inherent metabolism of the side chain. To clarify the metabolism of hydroxypropoxy substituent of the 2 beta-positon and a combination of metabolism between side chain and 2 beta-positon, four putative metabolites of ED-71 have been prepared as authentic samples. The metabolites at the 2 beta-positon, the methyl ester derivative considered as an ester standard of the oxidized metabolite and the tetraol derivative as the truncated metabolite were synthesized from alpha-epoxide, a key intermediate of ED-71 synthesis. The combination metabolites between side chain and 2 beta-positon, the 24(S)- and 24(R)-pentaols were synthesized using Trost's convergent method. (c) 2006 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2005.11.001
• 作为产物：
  描述：

  (4R,5R,6R)-5,6-dipivaloxy-1-(trimethylsilyl)oct-7-en-1-yn-4-ol 、 三乙基硅基三氟甲磺酸酯 在 sodium hydroxide 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 17.0h， 以93%的产率得到(3R,4R,5R)-3,4,5-tris(triethylsilyloxy)-oct-1-en-7-yne
  参考文献：
  名称：

  Synthesis of putative metabolites of 1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3 (ED-71)

  摘要：

  1 alpha,25-Dihydroxy-2 beta-(3-hydroxypropoxy)vitamin D-3 (ED-71), an analog of active vitamin D-3, 1 alpha,25-dihydroxyvitamin D-3 [1,25(OH)(2)D-3] is under phase III clinical trials in Japan for the treatment of osteoporosis and bone fracture prevention. Since ED-71 has a substituent at the 2 beta-position of the A-ring, it is recognized that the metabolic pathway of ED-71 might be more complicated than 1,25(OH)(2)D-3 because of metabolism at the 2 beta-position substituent in addition to the inherent metabolism of the side chain. To clarify the metabolism of hydroxypropoxy substituent of the 2 beta-positon and a combination of metabolism between side chain and 2 beta-positon, four putative metabolites of ED-71 have been prepared as authentic samples. The metabolites at the 2 beta-positon, the methyl ester derivative considered as an ester standard of the oxidized metabolite and the tetraol derivative as the truncated metabolite were synthesized from alpha-epoxide, a key intermediate of ED-71 synthesis. The combination metabolites between side chain and 2 beta-positon, the 24(S)- and 24(R)-pentaols were synthesized using Trost's convergent method. (c) 2006 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2005.11.001