methyl 8-(benzyloxycarbonylamino)-3-hydroxyoctanoate | 440353-67-3

• 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 8-(benzyloxycarbonylamino)-3-hydroxyoctanoate
• 英文别名: Methyl 3-hydroxy-8-(phenylmethoxycarbonylamino)octanoate
• CAS: 440353-67-3
• 化学式: C₁₇H₂₅NO₅
• 分子量: 323.389
• InChiKey: MBERMKTZCPJXNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 8-(benzyloxycarbonylamino)-3-hydroxyoctanoate 在 氢氧化钾 、 偶氮二甲酸二苄酯 、 盐酸羟胺 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 95.0h， 生成 N-acetoxy-4-(1-(5-benzyloxycarbonylamino)pentyl)-2-azetidinone
  参考文献：
  名称：

  An Enantioselective Synthesis of Differentially Protected erythro-α,β-Diamino Acids and Its Application to the Synthesis of an Analogue of Rhodopeptin B5

  摘要：

  Methodology for the enantioselective synthesis of differentially protected erythro-alpha,beta-diamino acids from N-tosyloxy beta-lactams is reported. The requisite N-tosyloxy beta-lactams are readily available from simple beta-keto esters. The reported approach is flexible and compatible with a variety of functional groups. The synthetic utility of the method is demonstrated through its application to the preparation of an analogue of the antifungal cyclic peptide rhodopeptin B5.

  DOI：

  10.1021/jo016276m
• 作为产物：
  描述：

  N-苄氧羰基--6-氨基己酸 在 sodium tetrahydroborate 、 二丁基镁 作用下， 以 四氢呋喃 、 甲醇 、 正庚烷 为溶剂， 反应 25.17h， 生成 methyl 8-(benzyloxycarbonylamino)-3-hydroxyoctanoate
  参考文献：
  名称：

  An Enantioselective Synthesis of Differentially Protected erythro-α,β-Diamino Acids and Its Application to the Synthesis of an Analogue of Rhodopeptin B5

  摘要：

  Methodology for the enantioselective synthesis of differentially protected erythro-alpha,beta-diamino acids from N-tosyloxy beta-lactams is reported. The requisite N-tosyloxy beta-lactams are readily available from simple beta-keto esters. The reported approach is flexible and compatible with a variety of functional groups. The synthetic utility of the method is demonstrated through its application to the preparation of an analogue of the antifungal cyclic peptide rhodopeptin B5.

  DOI：

  10.1021/jo016276m

文献信息

• An Enantioselective Synthesis of Differentially Protected <i>erythro</i>-α,β-Diamino Acids and Its Application to the Synthesis of an Analogue of Rhodopeptin B5
  作者：Timothy B. Durham、Marvin J. Miller

  DOI：10.1021/jo016276m

  日期：2003.1.1

  Methodology for the enantioselective synthesis of differentially protected erythro-alpha,beta-diamino acids from N-tosyloxy beta-lactams is reported. The requisite N-tosyloxy beta-lactams are readily available from simple beta-keto esters. The reported approach is flexible and compatible with a variety of functional groups. The synthetic utility of the method is demonstrated through its application to the preparation of an analogue of the antifungal cyclic peptide rhodopeptin B5.