methyl 2-[(2R,4S,5S)-4-hydroxy-5-[(2-methylpropan-2-yl)oxycarbonylamino]oxan-2-yl]acetate | 92143-26-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: methyl 2-[(2R,4S,5S)-4-hydroxy-5-[(2-methylpropan-2-yl)oxycarbonylamino]oxan-2-yl]acetate
• CAS: 92143-26-5
• 化学式: C₁₃H₂₃NO₆
• 分子量: 289.329
• InChiKey: RESOJQFQUDTWNC-UTLUCORTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.59
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  94.09
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  (3S,4S)-Methyl 4-<(tert-Butoxycarbonyl)amino>-3,5-bis<(tert-butyldimethylsilyl)oxy>pentanoate 在 四丁基氟化铵 、 二异丁基氢化铝 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 、 乙腈 为溶剂， 反应 41.0h， 生成 methyl 2-[(2R,4S,5S)-4-hydroxy-5-[(2-methylpropan-2-yl)oxycarbonylamino]oxan-2-yl]acetate
  参考文献：
  名称：

  Asymmetric intramolecular amidation of N-(tert-butoxycarbonyl)-3-hydroxy-4-pentenylamine. A new entry to chiral building blocks for the synthesis of biologically active nitrogen-containing compounds

  摘要：

  Sharpless reaction of racemic N-(tert-butoxycarbonyl)-3-hydroxy-4-pentenylamine (1) leads to both an asymmetric kinetic resolution to provide optically active 1, which was subsequently used for intramolecular amidomercuration, and asymmetric epoxidation followed by concomitant cyclization into optically active cis-3-hydroxy-2-(hydroxymethyl)pyrrolidine (3). Optically active 1 and 3 have been expediently used as chiral building blocks in the asymmetric synthesis of several biologically active natural products.

  DOI：

  10.1021/jo00001a045

文献信息

• Synthesis of (+)-galantinic acid, a constituent amino acid in the peptide antibiotic galantin I, the stereoselective epoxidation of a chiral serine equivalent
  作者：Yasufumi Ohfune、Natsuko Kurokawa

  DOI：10.1016/s0040-4039(01)90018-8

  日期：1984.1
• A New Synthetic Approach to (+)-Galantinic Acid, Degradation Product from the Peptide Antibiotic Galantin I, via 4-Amino-3-hydroxypyranose
  作者：Shinzo Kano、Tsutomu Yokomatsu、Shiroshi Shibuya

  DOI：10.3987/com-89-5207

  日期：——
• KANO, SHINZO;YOKOMATSU, TSUTOMU;SHIBUYA, SHIROSHI, HETEROCYCLES, 31,(1990) N, C. 13-16
  作者：KANO, SHINZO、YOKOMATSU, TSUTOMU、SHIBUYA, SHIROSHI

  DOI：——

  日期：——
• TAKAHATA, HIROKI;BANBA, YASUNORI;TAJIMA, MAYUMI;MOMOSE, TAKEFUMI, J. ORG. CHEM., 56,(1991) N, C. 240-245
  作者：TAKAHATA, HIROKI、BANBA, YASUNORI、TAJIMA, MAYUMI、MOMOSE, TAKEFUMI

  DOI：——

  日期：——