(3R,5R)-2-[5-(tert-butyldiphenylsilyl)-1-deoxy-2,3-O-isopropylidene-β-D-ribo-1,4-pentofuranos-1-yl]-5-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-azatriciclo[5.2.1.0^1,5]decane-4-carbonyl]-isoxazolidine-3-carboxylic acid ethyl ester | 455334-17-5

• 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: (3R,5R)-2-[5-(tert-butyldiphenylsilyl)-1-deoxy-2,3-O-isopropylidene-β-D-ribo-1,4-pentofuranos-1-yl]-5-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-azatriciclo[5.2.1.0^1,5]decane-4-carbonyl]-isoxazolidine-3-carboxylic acid ethyl ester
• 英文别名: ethyl (3R,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]-5-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decane-4-carbonyl]-1,2-oxazolidine-3-carboxylate；ethyl (3R,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]-5-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]decane-4-carbonyl]-1,2-oxazolidine-3-carboxylate
• CAS: 455334-17-5
• 化学式: C₄₁H₅₆N₂O₁₀SSi
• 分子量: 797.055
• InChiKey: YFYOCFRCWFKFFY-WNUXPJPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.11
• 重原子数：
  55
• 可旋转键数：
  11
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  139
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (3R,5R)-2-[5-(tert-butyldiphenylsilyl)-1-deoxy-2,3-O-isopropylidene-β-D-ribo-1,4-pentofuranos-1-yl]-5-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-azatriciclo[5.2.1.0^1,5]decane-4-carbonyl]-isoxazolidine-3-carboxylic acid ethyl ester 在 咪唑 、 盐酸 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 1-tert-butyl 2-ethyl (2R,4R)-4-[(tert-butyldiphenylsilyl)oxy]-5-oxo-pyrrolidine-1,2-dicarboxylate
  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 、 (R)-(-)-丙烯酰-2,10-樟脑磺内酰胺 、 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 40.0h， 以57%的产率得到(3R,5R)-2-[5-(tert-butyldiphenylsilyl)-1-deoxy-2,3-O-isopropylidene-β-D-ribo-1,4-pentofuranos-1-yl]-5-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-azatriciclo[5.2.1.0^1,5]decane-4-carbonyl]-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.