methyl (1S,2R,3R,4R,5S)-2,3-dihydroxy-4-methoxy-5-(phenylmethoxycarbonylamino)cyclopentane-1-carboxylate | 1169443-26-8

• 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: methyl (1S,2R,3R,4R,5S)-2,3-dihydroxy-4-methoxy-5-(phenylmethoxycarbonylamino)cyclopentane-1-carboxylate
• CAS: 1169443-26-8
• 化学式: C₁₆H₂₁NO₇
• 分子量: 339.345
• InChiKey: MWSFWKRXKOVVFX-ODXJTPSBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (1S,2R,3R,4R,5S)-2,3-dihydroxy-4-methoxy-5-(phenylmethoxycarbonylamino)cyclopentane-1-carboxylate 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 、 copper(II) sulfate 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以0.10 g的产率得到methyl (1S,2R,3R,4R,5S)-5-benzyloxycarbonylamino-2,3-isopropylidenedioxy-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：

  methyl (1S,2S,3R,4R,5R)-2-amino-4,5-dihydroxy-3-methoxycyclopentane-1-carboxylate 、 氯甲酸苄酯 在 碳酸氢钠 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 生成 methyl (1S,2R,3R,4R,5S)-2,3-dihydroxy-4-methoxy-5-(phenylmethoxycarbonylamino)cyclopentane-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