3-[(carboxymethyl)amino]-3-C-cyano-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranose | 1012796-19-8

• 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: 3-[(carboxymethyl)amino]-3-C-cyano-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranose
• CAS: 1012796-19-8
• 化学式: C₁₅H₂₂N₂O₇
• 分子量: 342.349
• InChiKey: FGWLZDGFZUNXJI-RZJSXJPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.05
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  119.27
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3-[(carboxymethyl)amino]-3-C-cyano-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranose 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以83%的产率得到(3R)-1,2:5,6-di-O-isopropylidene-spiro[3-deoxy-α-D-ribohexofuranose-3,5'-piperazine]-2'-one
  参考文献：
  名称：

  Novel glycine like amino acids from glyco-α-aminonitriles as building blocks for peptide synthesis

  摘要：

  Our interest in the glycoaminocyanation reaction led us to apply this methodology to introduce amino acids on a monosaccharide using the N-terminal position. The GAAs described in this paper are characterized by having the amino and carboxylic acid functionalities on a disubstituted position of the saccharide backbone leading to alpha,alpha-disubstituted glycines. These new sugar amino acids showed a restricted conformation involving a spontaneous intramolecular cyclization between the C- and N-terminal positions during hydrolysis or hydrogenolysis to give the corresponding oxopiperazine. Tripeptide mimics were obtained by the introduction of an additional amino acid using one-pot conditions starting from these cyclic by-products under basic media. We demonstrated that these pseudo tripeptides are good candidates for extension of the peptidic scaffold and cyclization. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.11.038
• 作为产物：
  描述：

  3-C-cyano-3-deoxy-1,2:5,6-di-O-isopropylidene-3-{[(methoxycarbonyl)methyl]amino}-α-D-allofuranose 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.67h， 以89%的产率得到3-[(carboxymethyl)amino]-3-C-cyano-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranose
  参考文献：
  名称：

  Novel glycine like amino acids from glyco-α-aminonitriles as building blocks for peptide synthesis

  摘要：

  Our interest in the glycoaminocyanation reaction led us to apply this methodology to introduce amino acids on a monosaccharide using the N-terminal position. The GAAs described in this paper are characterized by having the amino and carboxylic acid functionalities on a disubstituted position of the saccharide backbone leading to alpha,alpha-disubstituted glycines. These new sugar amino acids showed a restricted conformation involving a spontaneous intramolecular cyclization between the C- and N-terminal positions during hydrolysis or hydrogenolysis to give the corresponding oxopiperazine. Tripeptide mimics were obtained by the introduction of an additional amino acid using one-pot conditions starting from these cyclic by-products under basic media. We demonstrated that these pseudo tripeptides are good candidates for extension of the peptidic scaffold and cyclization. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.11.038