methyl (1S,2S,3R,4S,5R)-2-amino-4-hydroxy-3-methoxy-5-phenylmethoxycyclopentane-1-carboxylate | 1169443-11-1

• 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: methyl (1S,2S,3R,4S,5R)-2-amino-4-hydroxy-3-methoxy-5-phenylmethoxycyclopentane-1-carboxylate
• CAS: 1169443-11-1
• 化学式: C₁₅H₂₁NO₅
• 分子量: 295.335
• InChiKey: RTKPNCKKSMFKLZ-QSLWVIQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  91
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (1S,2S,3R,4S,5R)-2-amino-4-hydroxy-3-methoxy-5-phenylmethoxycyclopentane-1-carboxylate 、 氯甲酸苄酯 在 碳酸氢钠 作用下， 以 甲醇 、 水 为溶剂， 反应 6.0h， 以0.35 g的产率得到methyl (1S,2R,3S,4R,5S)-2-benzyloxy-5-benzyloxycarbonylamino-3-hydroxy-4-methoxy-cyclopentanecarboxylate
  参考文献：
  名称：

  Stereocontrolled transformation of nitrohexofuranoses into cyclopentylamines via 2-oxabicyclo[2.2.1]heptanes. IV: Synthesis of enantiopure methyl (1S,2R,3R,4R,5S)-5-benzyloxycarbonylamino-2,3-isopropylidenedioxy-4-methoxycyclopentanecarboxylate

  摘要：

  The first total synthesis of a new enantiopure polyhydroxylated cyclopentyl beta-amino acid [methyl (1S,2R,3S,4R,5S)-2-benzyloxy-5-benzyloxycarbonylamino-3-hydroxy-4-methoxycyclopentanecarboxylate] was achieved according to our recent novel strategy for the transformation of nitrohexofuranoses into cyclopentylamines. This approach is based on an intramolecular cyclization leading to 2-oxabicyclo[2.2.1]heptane derivatives. Epimerization of this amino acid derivative to methyl (1S,2R,3R,4R,5S)-2-benzyloxy-5-benzyloxycarbonylamino-3-hydroxy-4-methoxycyclopentanecarboxylate constitutes the first example of the preparation of one of the members of this family of amino acids with a stereochemistry that is not compatible with the above key cyclization step. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.03.004
• 作为产物：
  描述：

  甲醇 、 (1S,4S,5S,6R,7R)-7-benzyloxy-6-methoxy-5-nitro-2-oxabicyclo[2.2.1]heptan-3-one 在 氢气 、 镍 、 柠檬酸 作用下， 20.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 生成 methyl (1S,2S,3R,4S,5R)-2-amino-4-hydroxy-3-methoxy-5-phenylmethoxycyclopentane-1-carboxylate
  参考文献：
  名称：

  Stereocontrolled transformation of nitrohexofuranoses into cyclopentylamines via 2-oxabicyclo[2.2.1]heptanes. IV: Synthesis of enantiopure methyl (1S,2R,3R,4R,5S)-5-benzyloxycarbonylamino-2,3-isopropylidenedioxy-4-methoxycyclopentanecarboxylate

  摘要：

  The first total synthesis of a new enantiopure polyhydroxylated cyclopentyl beta-amino acid [methyl (1S,2R,3S,4R,5S)-2-benzyloxy-5-benzyloxycarbonylamino-3-hydroxy-4-methoxycyclopentanecarboxylate] was achieved according to our recent novel strategy for the transformation of nitrohexofuranoses into cyclopentylamines. This approach is based on an intramolecular cyclization leading to 2-oxabicyclo[2.2.1]heptane derivatives. Epimerization of this amino acid derivative to methyl (1S,2R,3R,4R,5S)-2-benzyloxy-5-benzyloxycarbonylamino-3-hydroxy-4-methoxycyclopentanecarboxylate constitutes the first example of the preparation of one of the members of this family of amino acids with a stereochemistry that is not compatible with the above key cyclization step. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.03.004