ethyl (3R,5R)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-methyl-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)isoxazolidine-5-carboxylate | 612806-76-5

• 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: ethyl (3R,5R)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-methyl-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)isoxazolidine-5-carboxylate
• 英文别名: ethyl (3R,5R)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-methyl-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-1,2-oxazolidine-5-carboxylate
• CAS: 612806-76-5
• 化学式: C₁₇H₂₅N₃O₇
• 分子量: 383.401
• InChiKey: YRQAAJPJLIDPCD-PSTGCABASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl (3R,5R)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-methyl-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)isoxazolidine-5-carboxylate 在 sodium periodate 、 对甲苯磺酸 作用下， 以 甲醇 、 水 为溶剂， 反应 6.0h， 生成 ethyl (3R,5R)-3-(hydroxymethyl)-2-methyl-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)isoxazolidine-5-carboxylate
  参考文献：
  名称：

  Enantioselective synthesis of N,O-psiconucleosides

  摘要：

  The first enantioselective synthesis Of beta-D and beta-L N,O-psiconucleosides is reported. The synthetic approach is based on the asymmetric 1.3-dipolar cycloaddition of the C-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-N-methyl nitrone with ethyl 2-acetyl-oxyacrylate followed by Vorbruggen nucleosidation, and removal of the chiral auxiliary. Stereochemical assignments are supported by a DFT theoretical study of the cycloaddition reaction. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00525-1
• 作为产物：
  描述：

  ethyl 2-(acetoxy)acrylate 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 30.0h， 生成 ethyl (3R,5R)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-methyl-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)isoxazolidine-5-carboxylate
  参考文献：
  名称：

  Enantioselective synthesis of N,O-psiconucleosides

  摘要：

  The first enantioselective synthesis Of beta-D and beta-L N,O-psiconucleosides is reported. The synthetic approach is based on the asymmetric 1.3-dipolar cycloaddition of the C-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-N-methyl nitrone with ethyl 2-acetyl-oxyacrylate followed by Vorbruggen nucleosidation, and removal of the chiral auxiliary. Stereochemical assignments are supported by a DFT theoretical study of the cycloaddition reaction. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00525-1

文献信息

• Enantioselective synthesis of N,O-psiconucleosides
  作者：Ugo Chiacchio、Luisa Borrello、Daniela Iannazzo、Pedro Merino、Anna Piperno、Antonio Rescifina、Barbara Richichi、Giovanni Romeo

  DOI：10.1016/s0957-4166(03)00525-1

  日期：2003.8

  The first enantioselective synthesis Of beta-D and beta-L N,O-psiconucleosides is reported. The synthetic approach is based on the asymmetric 1.3-dipolar cycloaddition of the C-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-N-methyl nitrone with ethyl 2-acetyl-oxyacrylate followed by Vorbruggen nucleosidation, and removal of the chiral auxiliary. Stereochemical assignments are supported by a DFT theoretical study of the cycloaddition reaction. (C) 2003 Elsevier Ltd. All rights reserved.