3-C-cyano-3-deoxy-1,2:5,6-di-O-isopropylidene-3-{[(S)-1-(methoxycarbonyl)-2-phenylethyl]amino}-α-D-allofuranose | 1012796-04-1

• 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-C-cyano-3-deoxy-1,2:5,6-di-O-isopropylidene-3-{[(S)-1-(methoxycarbonyl)-2-phenylethyl]amino}-α-D-allofuranose
• CAS: 1012796-04-1
• 化学式: C₂₃H₃₀N₂O₇
• 分子量: 446.5
• InChiKey: JNXCVDOIKMBVKQ-AXUDRJAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.65
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  108.27
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  3-C-cyano-3-deoxy-1,2:5,6-di-O-isopropylidene-3-{[(S)-1-(methoxycarbonyl)-2-phenylethyl]amino}-α-D-allofuranose 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以56%的产率得到(3R,3'S)-3'-benzyl-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：

  1,2:5,6-二-o-异亚丙基-alpha-d-ribo-3-己呋喃核糖 、 三甲基氰硅烷 、 L-苯丙氨酸甲酯盐酸盐 在 titanium(IV) isopropylate 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 17.0h， 以0.52 g的产率得到3-C-cyano-3-deoxy-1,2:5,6-di-O-isopropylidene-3-{[(S)-1-(methoxycarbonyl)-2-phenylethyl]amino}-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