(1S,3S,Z)-1,3-双TBS-O-TMS-马沙骨化醇 | 338956-90-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 中文名称: (1S,3S,Z)-1,3-双TBS-O-TMS-马沙骨化醇
• 中文别名: (1S,3S,Z)-1,3-双(叔丁基二甲基硅基)-O-三甲基硅基-马沙骨化醇
• 英文名称: (5Z,7E,1S,3S,20S)-1,3-bis(tert-butyldimethylsilyloxy)-20-(3-methyl-3-trimethylsilyloxybutyloxy)-9,10-secopregna-5,7,10(19)-triene
• 英文别名: [(1S,3Z,5S)-3-[(2E)-2-[(1S,3aS,7aS)-7a-methyl-1-[(1S)-1-(3-methyl-3-trimethylsilyloxybutoxy)ethyl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-5-[tert-butyl(dimethyl)silyl]oxy-2-methylidenecyclohexyl]oxy-tert-butyl-dimethylsilane
• CAS: 338956-90-4
• 化学式: C₄₁H₇₈O₄Si₃
• 分子量: 719.324
• InChiKey: DJNWLDIEJBFULF-HVMZRIQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.61
• 重原子数：
  48
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,3S,Z)-1,3-双TBS-O-TMS-马沙骨化醇 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以100%的产率得到3-Epi-1alpha,25-dihydroxy-22-oxavitamin D3
  参考文献：
  名称：

  Synthesis and evaluation of A-Ring diastereomers of 1α,25-dihydroxy-22-oxavitamin D 3 (OCT) 1

  摘要：

  A-ring diastereomers of 1 alpha ,25-dihydroxy-22-oxavitamin D-3 (OCT) (2), 3-epi-1 alpha ,25-dihydroxy-22-oxavitamin D-3 (3-epiOCT) (3) and 1,3-diepi-1 alpha ,25-dihydroxy-22-oxavitamin D-3 (1,3-diepiOCT) (4) were synthesized by the convergent method. In vitro binding affinity for rat vitamin D binding protein and calf-thymus vitamin D receptor, differentiation-inducing activity on HL-60 cells, and transcriptional activity of 3-epiOCT (3) and 1,3-diepiOCT (4) were evaluated in comparison with OCT (2), 1-epi-1 alpha ,25-dihydroxy-22-oxavitamin D-3 (1-epiOCT) (5) and 1 alpha ,25-dihydroxyvitamin D-3 (1). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00259-5
• 作为产物：
  描述：

  马沙骨化醇 在 正丁基锂 、 N-甲基吲哚酮 、 molecular sieve 、 四丙基高钌酸铵 、 碳酸氢钠 、 臭氧 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 11.0h， 生成 (1S,3S,Z)-1,3-双TBS-O-TMS-马沙骨化醇
  参考文献：
  名称：

  Synthesis and evaluation of A-Ring diastereomers of 1α,25-dihydroxy-22-oxavitamin D 3 (OCT) 1

  摘要：

  A-ring diastereomers of 1 alpha ,25-dihydroxy-22-oxavitamin D-3 (OCT) (2), 3-epi-1 alpha ,25-dihydroxy-22-oxavitamin D-3 (3-epiOCT) (3) and 1,3-diepi-1 alpha ,25-dihydroxy-22-oxavitamin D-3 (1,3-diepiOCT) (4) were synthesized by the convergent method. In vitro binding affinity for rat vitamin D binding protein and calf-thymus vitamin D receptor, differentiation-inducing activity on HL-60 cells, and transcriptional activity of 3-epiOCT (3) and 1,3-diepiOCT (4) were evaluated in comparison with OCT (2), 1-epi-1 alpha ,25-dihydroxy-22-oxavitamin D-3 (1-epiOCT) (5) and 1 alpha ,25-dihydroxyvitamin D-3 (1). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00259-5