(3R,5S)-5-(t-butyldiphenylsilyl)oxymethyl-3-hydroxy-N-benzyloxycarbonyl-pyrrolidine-2-one | 533923-48-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3R,5S)-5-(t-butyldiphenylsilyl)oxymethyl-3-hydroxy-N-benzyloxycarbonyl-pyrrolidine-2-one
• 英文别名: benzyl (3R,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-hydroxy-2-oxopyrrolidine-1-carboxylate
• CAS: 533923-48-7
• 化学式: C₂₉H₃₃NO₅Si
• 分子量: 503.67
• InChiKey: KFCYKSSTSIOMCM-JYFHCDHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.86
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,5S)-5-(t-butyldiphenylsilyl)oxymethyl-3-hydroxy-N-benzyloxycarbonyl-pyrrolidine-2-one 在 lithium hydroxide 、 ammonium hydroxide 、 四丁基氟化铵 、 N,N'-二环己基碳二亚胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， 反应 61.17h， 生成
  参考文献：
  名称：

  Probing the functional requirements of the l-haba side-chain of amikacin—synthesis, 16S A-site rRNA binding, and antibacterial activity

  摘要：

  The 1-amino group in amikacin was acylated with a variety of 2-hydroxy aminocarboxylic acids to probe the effect of acylation on ribosomal binding and antibacterial activity. The N-hydroxy urea analogue of amikacin (8a) in which the 2-S-hydroxyl-bearing carbon was replaced by an N-OH group was equally active against S. aureus and E. coli in vitro. The analogous tobramycin variant 9 was more active than amikacin. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01625-3
• 作为产物：
  描述：

  (S)-benzyl 2-(((tert-butyldiphenylsilyl)oxy)methyl)-5-oxopyrrolidine-1-carboxylate 在 lithium hexamethyldisilazane 、 (+)-8,8-二氯樟脑磺哑嗪 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 以36 mg的产率得到(3R,5S)-5-(t-butyldiphenylsilyl)oxymethyl-3-hydroxy-N-benzyloxycarbonyl-pyrrolidine-2-one
  参考文献：
  名称：

  Probing the functional requirements of the l-haba side-chain of amikacin—synthesis, 16S A-site rRNA binding, and antibacterial activity

  摘要：

  The 1-amino group in amikacin was acylated with a variety of 2-hydroxy aminocarboxylic acids to probe the effect of acylation on ribosomal binding and antibacterial activity. The N-hydroxy urea analogue of amikacin (8a) in which the 2-S-hydroxyl-bearing carbon was replaced by an N-OH group was equally active against S. aureus and E. coli in vitro. The analogous tobramycin variant 9 was more active than amikacin. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01625-3