(4S,5R)-3-(2-tert-Butoxycarbonylamino-2-methyl-propionyl)-5-methyl-2-oxo-oxazolidine-4-carboxylic acid benzyl ester | 879505-94-9

• 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-tert-Butoxycarbonylamino-2-methyl-propionyl)-5-methyl-2-oxo-oxazolidine-4-carboxylic acid benzyl ester
• 英文别名: Boc-Aib-N(For(1))Thr(1)-OBn；benzyl (4S,5R)-5-methyl-3-[2-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]-2-oxo-1,3-oxazolidine-4-carboxylate
• CAS: 879505-94-9
• 化学式: C₂₁H₂₈N₂O₇
• 分子量: 420.463
• InChiKey: JKRMBAYYXFUIFD-HIFRSBDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4S,5R)-3-(2-tert-Butoxycarbonylamino-2-methyl-propionyl)-5-methyl-2-oxo-oxazolidine-4-carboxylic acid benzyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以95%的产率得到(4S,5R)-3-(2-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
• 作为产物：
  描述：

  N-叔丁氧羰基-2-甲基丙氨酸 、 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 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以60%的产率得到(4S,5R)-3-(2-tert-Butoxycarbonylamino-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

文献信息

• Oxazolidin-2-one-Containing Pseudopeptides That Fold into β-Bend Ribbon Spirals
  作者：Claudia Tomasini、Gianluigi Luppi、Magda Monari

  DOI：10.1021/ja056762h

  日期：2006.2.1

  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.