(2S,3R,6R,7S)-7-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxy-4,8-dioxo-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid 4-nitro-benzyl ester | 208716-53-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3R,6R,7S)-7-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxy-4,8-dioxo-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid 4-nitro-benzyl ester
• 英文别名: (4-nitrophenyl)methyl (2S,3R,6R,7S)-7-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-3-hydroxy-4,8-dioxo-1-azabicyclo[4.2.0]octane-2-carboxylate
• CAS: 208716-53-4
• 化学式: C₂₃H₃₂N₂O₈Si
• 分子量: 492.601
• InChiKey: UHDWTAVFPKWCDF-GQJWIHHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  139
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,3R,6R,7S)-7-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxy-4,8-dioxo-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid 4-nitro-benzyl ester 在 potassium tri-sec-butyl-borohydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 (2S,3R,4S,6R,7S)-7-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,4-dihydroxy-8-oxo-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid 4-nitro-benzyl ester
  参考文献：
  名称：

  The oxidation induced rearrangement of carbapenems to carbacephams

  摘要：

  Upon dihydroxylation, carbapenems with an exocyclic vinyl sulfone at C-2 were found to rearrange to 2-keto-3-hydroxy carbacephams. These products could then be converted into the corresponding carbacephems. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00510-3
• 作为产物：
  描述：

  (4-nitrophenyl)methyl (2S,3Z,5R,6S)-6-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-3-[(4-fluorophenyl)sulfonylmethylidene]-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylate 在 四氧化锇 、 硫化氢 作用下， 生成 (2S,3R,6R,7S)-7-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxy-4,8-dioxo-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid 4-nitro-benzyl ester
  参考文献：
  名称：

  The oxidation induced rearrangement of carbapenems to carbacephams

  摘要：

  Upon dihydroxylation, carbapenems with an exocyclic vinyl sulfone at C-2 were found to rearrange to 2-keto-3-hydroxy carbacephams. These products could then be converted into the corresponding carbacephems. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00510-3