(2R,3R,5S)-5-Hydroxymethyl-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-phenylselanyl-pyrrolidine-1-carboxylic acid tert-butyl ester | 334024-82-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2R,3R,5S)-5-Hydroxymethyl-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-phenylselanyl-pyrrolidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2R,3R,5S)-5-(hydroxymethyl)-2-(5-methyl-2,4-dioxopyrimidin-1-yl)-3-phenylselanylpyrrolidine-1-carboxylate
• CAS: 334024-82-7
• 化学式: C₂₁H₂₇N₃O₅Se
• 分子量: 480.422
• InChiKey: KQOWGBXQOQGGOK-YXJHDRRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.16
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  99.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R,5S)-5-Hydroxymethyl-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-phenylselanyl-pyrrolidine-1-carboxylic acid tert-butyl ester 在 palladium on activated charcoal 氢气 、 双氧水 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 乙酸乙酯 为溶剂， 生成 aza-DDT
  参考文献：
  名称：

  Stereoselective synthesis of azanucleosides aza-stavudine (aza-D4T), aza-2′,3′-didehydro-3′-deoxyuridine (aza-D4U), and its hydrogenated analogues from an endocyclic enecarbamate

  摘要：

  The stereoselective synthesis of the aza-analogues of nucleosides stavudine (D4T) and dideoxyuridine (DDU) were accomplished in a very concise manner (3-4 step sequences) with high overall yields from a five-membered endocyclic enecarbamate employing phenylselenenyl bromide as an effective promoter. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02343-1
• 作为产物：
  描述：

  5-甲基-1,3-二(三甲基硅烷基)-2,4(1H,3H)-嘧啶二酮 在 zinc dibromide 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 生成 (2R,3R,5S)-5-Hydroxymethyl-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-phenylselanyl-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Stereoselective synthesis of azanucleosides aza-stavudine (aza-D4T), aza-2′,3′-didehydro-3′-deoxyuridine (aza-D4U), and its hydrogenated analogues from an endocyclic enecarbamate

  摘要：

  The stereoselective synthesis of the aza-analogues of nucleosides stavudine (D4T) and dideoxyuridine (DDU) were accomplished in a very concise manner (3-4 step sequences) with high overall yields from a five-membered endocyclic enecarbamate employing phenylselenenyl bromide as an effective promoter. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02343-1

文献信息

• Stereoselective synthesis of azanucleosides aza-stavudine (aza-D4T), aza-2′,3′-didehydro-3′-deoxyuridine (aza-D4U), and its hydrogenated analogues from an endocyclic enecarbamate
  作者：Edson R Costenaro、Luis A.M Fontoura、Denilson F Oliveira、Carlos R.D Correia

  DOI：10.1016/s0040-4039(00)02343-1

  日期：2001.2

  The stereoselective synthesis of the aza-analogues of nucleosides stavudine (D4T) and dideoxyuridine (DDU) were accomplished in a very concise manner (3-4 step sequences) with high overall yields from a five-membered endocyclic enecarbamate employing phenylselenenyl bromide as an effective promoter. (C) 2001 Elsevier Science Ltd. All rights reserved.