(3S,5R)-5-acetyl-2-[5-(tert-butyldiphenylsilyl)-1-deoxy-2,3-O-isopropylidene-β-D-ribo-1,4-pentofuranos-1-yl]-isoxazolidine-3-carboxylic acid ethyl ester | 455334-18-6

• 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: (3S,5R)-5-acetyl-2-[5-(tert-butyldiphenylsilyl)-1-deoxy-2,3-O-isopropylidene-β-D-ribo-1,4-pentofuranos-1-yl]-isoxazolidine-3-carboxylic acid ethyl ester
• 英文别名: 3-O-ethyl 5-O-methyl (3S,5R)-2-[(3aR,4R,6R,6aR)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-1,2-oxazolidine-3,5-dicarboxylate
• CAS: 455334-18-6
• 化学式: C₃₂H₄₃NO₉Si
• 分子量: 613.78
• InChiKey: CHAGKTHKPRKCGI-REAMANMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (3S,5R)-5-acetyl-2-[5-(tert-butyldiphenylsilyl)-1-deoxy-2,3-O-isopropylidene-β-D-ribo-1,4-pentofuranos-1-yl]-isoxazolidine-3-carboxylic acid ethyl ester 在 咪唑 、 盐酸 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (2S,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-oxo-pyrrolidine-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Enantioselective synthesis of 4-hydroxy-d-pyroglutamic acid derivatives by an asymmetric 1,3-dipolar cycloaddition

  摘要：

  The 1,3-dipolar cycloaddition of a chiral nitrone derived from glyoxylic acid and protected D-ribosyl hydroxylamine with the acrylamide of Oppolzer's sultam provides a perfectly stereoselective approach to protected (2R,4R)-4-hydroxy-D-pyro-lutamic acid. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00072-1
• 作为产物：
  描述：

  乙醛酸乙酯 、 丙烯酸甲酯（MA） 、 5-(tert-butyldiphenylsilyl)-1-deoxy-1-hydroxyamino-2,3-O-isopropylidene-β-D-ribo-1,4-pentofuranose 以 甲苯 为溶剂， 反应 18.0h， 以53%的产率得到(3R,5R)-5-acetyl-2-[5-(tert-butyldiphenylsilyl)-1-deoxy-2,3-O-isopropylidene-β-D-ribo-1,4-pentofuranos-1-yl]-isoxazolidine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Enantioselective synthesis of 4-hydroxy-d-pyroglutamic acid derivatives by an asymmetric 1,3-dipolar cycloaddition

  摘要：

  The 1,3-dipolar cycloaddition of a chiral nitrone derived from glyoxylic acid and protected D-ribosyl hydroxylamine with the acrylamide of Oppolzer's sultam provides a perfectly stereoselective approach to protected (2R,4R)-4-hydroxy-D-pyro-lutamic acid. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00072-1

文献信息

• Enantioselective synthesis of 4-hydroxy-d-pyroglutamic acid derivatives by an asymmetric 1,3-dipolar cycloaddition
  作者：Pedro Merino、Julia Revuelta、Tomas Tejero、Ugo Chiacchio、Antonio Rescifina、Anna Piperno、Giovanni Romeo

  DOI：10.1016/s0957-4166(02)00072-1

  日期：2002.2

  The 1,3-dipolar cycloaddition of a chiral nitrone derived from glyoxylic acid and protected D-ribosyl hydroxylamine with the acrylamide of Oppolzer's sultam provides a perfectly stereoselective approach to protected (2R,4R)-4-hydroxy-D-pyro-lutamic acid. (C) 2002 Elsevier Science Ltd. All rights reserved.