5-O-benzyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-{[(methoxycarbonyl)methyl]amino}-α-D-ribofuranose | 1012796-05-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-O-benzyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-{[(methoxycarbonyl)methyl]amino}-α-D-ribofuranose
• CAS: 1012796-05-2
• 化学式: C₁₉H₂₄N₂O₆
• 分子量: 376.409
• InChiKey: MQKYBFCYMUCEJR-NOCIGQNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  99.04
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  5-O-benzyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-{[(methoxycarbonyl)methyl]amino}-α-D-ribofuranose 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以54%的产率得到(3R)-5-O-benzyl-1,2-O-isopropylidene-spiro[3-deoxy-α-D-erythro-pentofuranose-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：

  5-O-benzyl-3-oxo-1,2-O-isopropylidene-α-D-xylofuranose 、 三甲基氰硅烷 、 甘氨酸甲酯盐酸盐 在 titanium(IV) isopropylate 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 17.0h， 以4.93 g的产率得到5-O-benzyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-{[(methoxycarbonyl)methyl]amino}-α-D-ribofuranose
  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