(2S,3R,4S)-2-azidomethyl-1-benzyl-3,4-(O-isopropylidene)dihydroxypyrrolidine | 176218-82-9

• 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: (2S,3R,4S)-2-azidomethyl-1-benzyl-3,4-(O-isopropylidene)dihydroxypyrrolidine
• 英文别名: (2S,3R,4S)-2-Azidomethyl-1-benzyl-3,4-(isopropylidenedioxy)pyrrolidine；(3aR,4S,6aS)-4-(azidomethyl)-5-benzyl-2,2-dimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole
• CAS: 176218-82-9
• 化学式: C₁₅H₂₀N₄O₂
• 分子量: 288.349
• InChiKey: MFRNPUMJKNBWKE-MELADBBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  36.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S)-2-azidomethyl-1-benzyl-3,4-(O-isopropylidene)dihydroxypyrrolidine 在 palladium on activated charcoal 氢气 作用下， 50.0 ℃ 、344.73 kPa 条件下， 反应 3.0h， 以99%的产率得到C-((3aR,4S,6aS)-2,2-Dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl)-methylamine
  参考文献：
  名称：

  Synthesis and in vitro cytotoxicity of cis-dichloro[(2S,3R,4S)-2-aminomethyl-3,4-(O-isopropylidene)dihydroxy- or -3,4-dihydroxypyrrolidine]platinum(II)

  摘要：

  cis-Dichloro[(2S,3R,4S)-2-aminomethyl-3,4-(O-isopropylidene)dihydroxypyrrolidine]platinum(II) (1) and cis-dichloro [(2S,3R,4S)-2-aminomethyl-3,4-dihydroxypyrrolidine]platinum(II) (2) have been synthesized and evaluated for their in vitro cytotoxicity against cisplatin-sensitive and -resistant L1210 murine leukemia cell lines and human tumor cell lines. complex I showed high cytotoxicity against human cancer cell lines, A 549, SK-OV-3, and XF 498 and much lower cross-resistance against cisplatin-resistant L1210 cells than cisplatin and carboplatin.

  DOI：

  10.1016/0960-894x(96)00088-1
• 作为产物：
  描述：

  5-(tert-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-D-ribofuranose 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 sodium azide 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 33.0h， 生成 (2S,3R,4S)-2-azidomethyl-1-benzyl-3,4-(O-isopropylidene)dihydroxypyrrolidine
  参考文献：
  名称：

  Preparation of optically active 3-substituted piperidines via ring expansion: synthesis of 4-amino- and 4-fluoro-1,4,5-trideoxy-1,5-imino-D-ribitol and 1,5-dideoxy-1,5-imino-D-ribitol

  摘要：

  介绍了一种基于 1-苄基-2-(甲磺酰氧基甲基)吡咯烷 13 与各种亲核剂的扩环作用制备光学活性 3-取代 1-苄基哌啶的新方法。4- 氨基-1,4,5-三脱氧-1,5-亚氨基-D-核糖醇 5、1,4,5-三脱氧-4-氟-1,5-亚氨基-D-核糖醇 6 和 1,5-二脱氧-1,5-亚氨基-D-核糖醇 7 也是通过化合物 13 扩环的路线合成的。

  DOI：

  10.1039/p19960000803

文献信息

• Preparation of optically active 3-substituted piperidines via ring expansion: synthesis of 4-amino- and 4-fluoro-1,4,5-trideoxy-1,5-imino-D-ribitol and 1,5-dideoxy-1,5-imino-D-ribitol
  作者：Dae-Kee Kim、Ganghyeok Kim、Young-Woo Kim

  DOI：10.1039/p19960000803

  日期：——

  A new method for the preparation of optically active 3-substituted 1-benzylpiperidines based on the ring expansion of the 1-benzyl-2-(methylsulfonyloxymethyl)pyrrolidine 13 with various nucleophiles has been described. Synthesis of 4-amino-1,4,5-trideoxy-1,5-imino-D-ribitol 5,1,4,5-trideoxy-4-fluoro-1,5-imino-D-ribitol 6 and 1,5-dideoxy-1,5-imino-D-ribitol 7 has also been achieved by a route which involves ring expansion of compound 13.

  介绍了一种基于 1-苄基-2-(甲磺酰氧基甲基)吡咯烷 13 与各种亲核剂的扩环作用制备光学活性 3-取代 1-苄基哌啶的新方法。4- 氨基-1,4,5-三脱氧-1,5-亚氨基-D-核糖醇 5、1,4,5-三脱氧-4-氟-1,5-亚氨基-D-核糖醇 6 和 1,5-二脱氧-1,5-亚氨基-D-核糖醇 7 也是通过化合物 13 扩环的路线合成的。
• Synthesis and in vitro cytotoxicity of cis-dichloro[(2S,3R,4S)-2-aminomethyl-3,4-(O-isopropylidene)dihydroxy- or -3,4-dihydroxypyrrolidine]platinum(II)
  作者：Dae-Kee Kim、Young-Woo Kim、Hun-Taek Kim、Key H. Kim

  DOI：10.1016/0960-894x(96)00088-1

  日期：1996.3

  cis-Dichloro[(2S,3R,4S)-2-aminomethyl-3,4-(O-isopropylidene)dihydroxypyrrolidine]platinum(II) (1) and cis-dichloro [(2S,3R,4S)-2-aminomethyl-3,4-dihydroxypyrrolidine]platinum(II) (2) have been synthesized and evaluated for their in vitro cytotoxicity against cisplatin-sensitive and -resistant L1210 murine leukemia cell lines and human tumor cell lines. complex I showed high cytotoxicity against human cancer cell lines, A 549, SK-OV-3, and XF 498 and much lower cross-resistance against cisplatin-resistant L1210 cells than cisplatin and carboplatin.