(2,4-dioxo-3-azaspiro[5.5]undecan-3-yl) (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate | 1280225-71-9

• 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: (2,4-dioxo-3-azaspiro[5.5]undecan-3-yl) (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 1280225-71-9
• 化学式: C₁₈H₂₈N₂O₆
• 分子量: 368.43
• InChiKey: LMTLSOCNIQUZKJ-LBPRGKRZSA-N

物化性质

• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  L-丙氨酸 、 (2,4-dioxo-3-azaspiro[5.5]undecan-3-yl) (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate 在 sodium carbonate 、 potassium hydrogensulfate 作用下， 以 水 、 四氢呋喃 为溶剂， 反应 10.08h， 以74%的产率得到叔丁氧羰基-丙氨酰-丙氨酸
  参考文献：
  名称：

  Synthesis of dipeptides from N-hydroxy-3-azaspiro[5,5]undecane-2,4-dione activated α-amino acids

  摘要：

  A simple two step procedure for the synthesis of a dipeptide from N-hydroxy-3-azaspiro[5,5]undecane-2,4-dione (HO-ASUD) activated a-amino acids is described. In presence of DCC, N-hydroxy-3-azaspiro[5,5]undecane-2,4-dione readily esterifies the carboxylic acid group of all the N-protected amino acids to yield crystalline N-hydroxy-3-aza spiro[5,5]undecane-2,4-dione activated carboxy ester. The N-hydroxy-3-aza spiro[5,5]undecane-2,4-dione activated carboxy esters of N-protected amino acids readily condensed with other amino acids and gave a dipeptide. This new method is effective for the DCC coupling of a variety of chiral amino acids without loss of enantiomeric purity. Synthesis of fifteen dipeptides including the hitherto unreported Fmoc-L-Orn(Boc)-Val-OMe. Fmoc-L-Cys(trt)-Gly-OEt and Boc-L-Tyr-Gly-OEt is presented. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.12.021
• 作为产物：
  描述：

  N-羟基-3,3-环戊烷戊二酰亚胺 、 N-叔丁氧羰基-L-丙氨酸 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以100%的产率得到(2,4-dioxo-3-azaspiro[5.5]undecan-3-yl) (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
  参考文献：
  名称：

  Synthesis of dipeptides from N-hydroxy-3-azaspiro[5,5]undecane-2,4-dione activated α-amino acids

  摘要：

  A simple two step procedure for the synthesis of a dipeptide from N-hydroxy-3-azaspiro[5,5]undecane-2,4-dione (HO-ASUD) activated a-amino acids is described. In presence of DCC, N-hydroxy-3-azaspiro[5,5]undecane-2,4-dione readily esterifies the carboxylic acid group of all the N-protected amino acids to yield crystalline N-hydroxy-3-aza spiro[5,5]undecane-2,4-dione activated carboxy ester. The N-hydroxy-3-aza spiro[5,5]undecane-2,4-dione activated carboxy esters of N-protected amino acids readily condensed with other amino acids and gave a dipeptide. This new method is effective for the DCC coupling of a variety of chiral amino acids without loss of enantiomeric purity. Synthesis of fifteen dipeptides including the hitherto unreported Fmoc-L-Orn(Boc)-Val-OMe. Fmoc-L-Cys(trt)-Gly-OEt and Boc-L-Tyr-Gly-OEt is presented. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.12.021

文献信息

• 3-Azaspiro[5,5]undecan-2,4-dioxo-3-yl diphenyl phosphate (ASUD-diphenyl phosphate), a new reagent for the synthesis of the N-protected amino acid-ASUD ester
  作者：B. Leelamaheswara Rao、Shaik Nowshuddin、Anjali Jha、Murali K. Divi、M.N.A. Rao

  DOI：10.1016/j.tetasy.2016.04.007

  日期：2016.7

  A new reagent, 3-azaspiro[5,5]undecan-2,4-dioxo-3-yl diphenyl phosphate (ASUD-diphenyl phosphate) is described for the synthesis of N-protected amino acid-ASUD esters which are active esters useful in the synthesis of peptides. This compound was synthesized by reacting N-hydroxy-3-azaspiro[5,5]-undecane-2,4-dione (HO-ASUD) with diphenyl chlorophosphate in the presence of a base at room temperature and was obtained in high yields. The ASUD-diphenyl phosphate reagent reacts with N-protected amino acids under mild conditions to give the corresponding ASUD active esters, while preserving the enantiomeric purity of the amino acid. The new reagent is a stable crystalline compound and eliminates the need for DCC, a potent skin allergen, used previously for the synthesis of N-protected amino acid-ASUD ester. (C) 2016 Elsevier Ltd. All rights reserved.