1-[(3R,5S,8S,9S,10R,13S,14S,17S)-3-(tert-Butyl-dimethyl-silanyloxy)-10,13-dimethyl-hexadecahydro-6-oxa-cyclopenta[a]phenanthren-17-yl]-ethanone | 282091-44-5

• 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
• 英文名称: 1-[(3R,5S,8S,9S,10R,13S,14S,17S)-3-(tert-Butyl-dimethyl-silanyloxy)-10,13-dimethyl-hexadecahydro-6-oxa-cyclopenta[a]phenanthren-17-yl]-ethanone
• CAS: 282091-44-5
• 化学式: C₂₆H₄₆O₃Si
• 分子量: 434.735
• InChiKey: HPSCQNXHJHPFEK-NXSMROTCSA-N

反应信息

• 作为反应物：
  描述：

  1-[(3R,5S,8S,9S,10R,13S,14S,17S)-3-(tert-Butyl-dimethyl-silanyloxy)-10,13-dimethyl-hexadecahydro-6-oxa-cyclopenta[a]phenanthren-17-yl]-ethanone 在 氢氟酸 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 5.5h， 以0.156 g的产率得到3α-hydroxy-6-oxa-5α-pregnan-20-one
  参考文献：
  名称：

  Synthesis and GABAA receptor activity of 6-oxa-analogs of neurosteroids

  摘要：

  The 6-oxasteroids 3 alpha-hydroxy-6-oxa-5 alpha-pregnan-20-one (3) and 3 alpha-hydroxy-6-oxa-5 beta-pregnan-20-one (4) were obtained from pregnenolone acetate via the corresponding (5 alpha or 5 beta) 3 beta,20 beta-diacetoxy-6-oxa-pregnane. Both steroids showed ca. 100-fold reduced potency for modulating [H-3]flunitrazepam, [H-3]muscimol or [S-35]TBPS binding to the GABA(A) receptor when compared to their natural carbon analogs 3 alpha-hydroxy-5 alpha-pregnan-20-one (1) and 3 alpha-hydroxy-5 beta-pregnan-20-one (2). (C) 2000 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(00)00088-x
• 作为产物：
  描述：

  Acetic acid (S)-1-((3R,5S,8S,9S,10R,13S,14S,17S)-3-formyloxy-10,13-dimethyl-hexadecahydro-6-oxa-cyclopenta[a]phenanthren-17-yl)-ethyl ester 在 咪唑 、 lithium aluminium tetrahydride 、 3 A molecular sieve 、 potassium hydrogencarbonate 、 barium carbonate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 生成 1-[(3R,5S,8S,9S,10R,13S,14S,17S)-3-(tert-Butyl-dimethyl-silanyloxy)-10,13-dimethyl-hexadecahydro-6-oxa-cyclopenta[a]phenanthren-17-yl]-ethanone
  参考文献：
  名称：

  Synthesis and GABAA receptor activity of 6-oxa-analogs of neurosteroids

  摘要：

  The 6-oxasteroids 3 alpha-hydroxy-6-oxa-5 alpha-pregnan-20-one (3) and 3 alpha-hydroxy-6-oxa-5 beta-pregnan-20-one (4) were obtained from pregnenolone acetate via the corresponding (5 alpha or 5 beta) 3 beta,20 beta-diacetoxy-6-oxa-pregnane. Both steroids showed ca. 100-fold reduced potency for modulating [H-3]flunitrazepam, [H-3]muscimol or [S-35]TBPS binding to the GABA(A) receptor when compared to their natural carbon analogs 3 alpha-hydroxy-5 alpha-pregnan-20-one (1) and 3 alpha-hydroxy-5 beta-pregnan-20-one (2). (C) 2000 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(00)00088-x