(4S,5R)-3-(2-{[(4S,5R)-3-(2-tert-Butoxycarbonylamino-2-methyl-propionyl)-5-methyl-2-oxo-oxazolidine-4-carbonyl]-amino}-2-methyl-propionyl)-5-methyl-2-oxo-oxazolidine-4-carboxylic acid benzyl ester | 879505-97-2

• 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: (4S,5R)-3-(2-{[(4S,5R)-3-(2-tert-Butoxycarbonylamino-2-methyl-propionyl)-5-methyl-2-oxo-oxazolidine-4-carbonyl]-amino}-2-methyl-propionyl)-5-methyl-2-oxo-oxazolidine-4-carboxylic acid benzyl ester
• 英文别名: Boc-Aib-N(For(1))Thr(1)-Aib-N(For(2))Thr(2)-OBn；benzyl (4S,5R)-5-methyl-3-[2-methyl-2-[[(4S,5R)-5-methyl-3-[2-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]-2-oxo-1,3-oxazolidine-4-carbonyl]amino]propanoyl]-2-oxo-1,3-oxazolidine-4-carboxylate
• CAS: 879505-97-2
• 化学式: C₃₀H₄₀N₄O₁₁
• 分子量: 632.668
• InChiKey: IITWCNSAXTUUOU-JYBIWHBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  45
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  187
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (4S,5R)-3-(2-{[(4S,5R)-3-(2-tert-Butoxycarbonylamino-2-methyl-propionyl)-5-methyl-2-oxo-oxazolidine-4-carbonyl]-amino}-2-methyl-propionyl)-5-methyl-2-oxo-oxazolidine-4-carboxylic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以100%的产率得到(4S,5R)-3-(2-{[(4S,5R)-3-(2-tert-Butoxycarbonylamino-2-methyl-propionyl)-5-methyl-2-oxo-oxazolidine-4-carbonyl]-amino}-2-methyl-propionyl)-5-methyl-2-oxo-oxazolidine-4-carboxylic acid
  参考文献：
  名称：

  Oxazolidin-2-one-Containing Pseudopeptides That Fold into β-Bend Ribbon Spirals

  摘要：

  Three sets of oligomers containing the 4-carboxy-5-methyloxazolidin-2-one (Oxd) moiety have been synthesized with the aim of checking whether these molecules are able to fold in ordered structures: A set [Boc-(L-Ala-L-Oxd),-OR], B set [BOC-(L-Ala-D-Oxd)(n)-OR], and C set [Boc-(Aib-L-Oxd)(n)-OR] preferential conformations have been analyzed with IR absorption, NMR, and CID. We have noticed that in these oligomers three stabilizing effects are active: (i) the rigid Oxd -CO-N(CH <)-CO- moiety, which always tend to assume a trans conformation; (ii) the formation of Oxd C=(OH)-H-...-C-alpha intramolecolar H-bonds; (iii) the alternate formation of 1 - 4 intramolecular C=(OH)-H-...-N H-bonds. Through the analysis of the experimental data, we could demonstrate that only the oligomers of the B set are able to meet all three requirements listed above. By a deeper insight into the CD spectra, we gathered that the secondary structure adopted by the B set oligomers is a beta-bend ribbon spiral, which is a subtype of the 3(10)-helix.

  DOI：

  10.1021/ja056762h
• 作为产物：
  描述：

  benzyl (4S,5R)-5-methyl-2-oxo-1,3-oxazolidine-4-carboxylate 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 5.17h， 生成 (4S,5R)-3-(2-{[(4S,5R)-3-(2-tert-Butoxycarbonylamino-2-methyl-propionyl)-5-methyl-2-oxo-oxazolidine-4-carbonyl]-amino}-2-methyl-propionyl)-5-methyl-2-oxo-oxazolidine-4-carboxylic acid benzyl ester
  参考文献：
  名称：

  Oxazolidin-2-one-Containing Pseudopeptides That Fold into β-Bend Ribbon Spirals

  摘要：

  Three sets of oligomers containing the 4-carboxy-5-methyloxazolidin-2-one (Oxd) moiety have been synthesized with the aim of checking whether these molecules are able to fold in ordered structures: A set [Boc-(L-Ala-L-Oxd),-OR], B set [BOC-(L-Ala-D-Oxd)(n)-OR], and C set [Boc-(Aib-L-Oxd)(n)-OR] preferential conformations have been analyzed with IR absorption, NMR, and CID. We have noticed that in these oligomers three stabilizing effects are active: (i) the rigid Oxd -CO-N(CH <)-CO- moiety, which always tend to assume a trans conformation; (ii) the formation of Oxd C=(OH)-H-...-C-alpha intramolecolar H-bonds; (iii) the alternate formation of 1 - 4 intramolecular C=(OH)-H-...-N H-bonds. Through the analysis of the experimental data, we could demonstrate that only the oligomers of the B set are able to meet all three requirements listed above. By a deeper insight into the CD spectra, we gathered that the secondary structure adopted by the B set oligomers is a beta-bend ribbon spiral, which is a subtype of the 3(10)-helix.

  DOI：

  10.1021/ja056762h