(Z,3S,5S)-2-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]-1-chloroethane | 216380-59-5

• 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: (Z,3S,5S)-2-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]-1-chloroethane
• 英文别名: tert-butyl-[(1S,3S,5Z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-chloroethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane
• CAS: 216380-59-5
• 化学式: C₂₁H₄₁ClO₂Si₂
• 分子量: 417.179
• InChiKey: LMDOYFASUNIFPL-OVVXSAMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.28
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z,3S,5S)-2-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]-1-chloroethane 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 7.67h， 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
• 作为产物：
  描述：

  (Z,3S,5S)-2-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]ethanol 在 N-氯代丁二酰亚胺 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到(Z,3S,5S)-2-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]-1-chloroethane
  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

文献信息

• Synthesis and evaluation of A-Ring diastereomers of 1α,25-dihydroxy-22-oxavitamin D 3 (OCT) 1
  作者：Susumi Hatakeyama、Toshio Okano、Junji Maeyama、Tomoyuki Esumi、Hiroko Hiyamizu、Yoshiharu Iwabuchi、Kimie Nakagawa、Keiichi Ozono、Akira Kawase、Noboru Kubodera

  DOI：10.1016/s0968-0896(00)00259-5

  日期：2001.2

  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.