benzyl L-2-<(benzyloxycarbonyl)amino>-5-tosyloxypentanoate | 167319-90-6

• 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: benzyl L-2-<(benzyloxycarbonyl)amino>-5-tosyloxypentanoate
• 英文别名: benzyl (2S)-5-(4-methylphenyl)sulfonyloxy-2-(phenylmethoxycarbonylamino)pentanoate
• CAS: 167319-90-6
• 化学式: C₂₇H₂₉NO₇S
• 分子量: 511.596
• InChiKey: HZGSONMPELKEBA-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.52
• 重原子数：
  36.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  108.0
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  benzyl L-2-<(benzyloxycarbonyl)amino>-5-tosyloxypentanoate 在 盐酸 、 sodium hydroxide 、 硫化氢 、 sodium hydride 、 copper(II) oxide 、 zinc(II) chloride 作用下， 以 乙醇 为溶剂， 反应 31.5h， 生成 L-2-amino-5-(guanidinooxy)pentanoic acid
  参考文献：
  名称：

  Insecticidal properties of some derivatives of L-canavanine

  摘要：

  The canavanine derivatives D-canavanine and L-homocanavanine as well as the 1-methyl and 1-ethyl esters of L-canavanine were synthesized and evaluated for biological activity in fifth instar larvae of the tobacco hornworm, Manduca sexta [Sphingidae]. While L-homocanavanine did not increase intrinsic toxicity, it was as deleterious as L-canavanine. D-Canavanine was biologically active, as demonstrated by its ability to cause larval edema, but the D-enantiomer had little ability to elicit the larval growth inhibition and pupal deformity which are hallmarks of canavanine toxicosis and was postulated to be linked to aberrant protein production. The 1-methyl and 1-ethyl esters of L-canavanine were synthesized to determine if enhancing canavanine's hydrophobicity might increase its bioavailability. Our experiments revealed that these esters are less toxic than canavanine; the ethyl ester disrupted larval growth more than did the methyl analogue.

  DOI：

  10.1021/jf00058a034
• 作为产物：
  描述：

  L-<(2-benzyloxycarbonyl)amino>-5-hydroxypentanoic acid 在 sodium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 23.0h， 生成 benzyl L-2-<(benzyloxycarbonyl)amino>-5-tosyloxypentanoate
  参考文献：
  名称：

  Insecticidal properties of some derivatives of L-canavanine

  摘要：

  The canavanine derivatives D-canavanine and L-homocanavanine as well as the 1-methyl and 1-ethyl esters of L-canavanine were synthesized and evaluated for biological activity in fifth instar larvae of the tobacco hornworm, Manduca sexta [Sphingidae]. While L-homocanavanine did not increase intrinsic toxicity, it was as deleterious as L-canavanine. D-Canavanine was biologically active, as demonstrated by its ability to cause larval edema, but the D-enantiomer had little ability to elicit the larval growth inhibition and pupal deformity which are hallmarks of canavanine toxicosis and was postulated to be linked to aberrant protein production. The 1-methyl and 1-ethyl esters of L-canavanine were synthesized to determine if enhancing canavanine's hydrophobicity might increase its bioavailability. Our experiments revealed that these esters are less toxic than canavanine; the ethyl ester disrupted larval growth more than did the methyl analogue.

  DOI：

  10.1021/jf00058a034