benzyl D-2-<(benzyloxycarbonyl)amino>-4-hydroxybutyrate | 167319-97-3

• 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 D-2-<(benzyloxycarbonyl)amino>-4-hydroxybutyrate
• 英文别名: N-benzyloxycarbonyl-S-homoserine benzyl ester；benzyl (2R)-4-hydroxy-2-(phenylmethoxycarbonylamino)butanoate
• CAS: 167319-97-3
• 化学式: C₁₉H₂₁NO₅
• 分子量: 343.379
• InChiKey: NCSXKRHKIBFUQI-QGZVFWFLSA-N

物化性质

• 沸点：
  540.3±50.0 °C(Predicted)
• 密度：
  1.230±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  84.86
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  benzyl D-2-<(benzyloxycarbonyl)amino>-4-hydroxybutyrate 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以38%的产率得到N-benzyloxycarbonyl-D-homoserine aldehyde benzyl ester
  参考文献：
  名称：

  [EN] COMBINATION THERAPY WITH INHIBITORS OF INDUCIBLE NITRIC OXIDE SYNTHASE AND ALKYLATING AGENTS
  [FR] THERAPIE DE COMBINAISON AVEC DES INHIBITEURS DE LA SYNTHASE DU MONOXYDE D'AZOTE INDUCTIBLE ET DES AGENTS D'ALKYLATION

  摘要：

  公开号：

  WO2005025620A3
• 作为产物：
  描述：

  (R)-2-氧代四氢呋喃-3-基氨基甲酸苄酯 在 sodium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 benzyl D-2-<(benzyloxycarbonyl)amino>-4-hydroxybutyrate
  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

文献信息

• [EN] METHODS FOR TREATMENT AND PREVENTION OF GASTROINTESTINAL CONDITIONS<br/>[FR] PROCEDES DESTINES AU TRAITEMENT ET A LA PREVENTION DE TROUBLES GASTRO-INTESTINAUX
  申请人：PHARMACIA CORP

  公开号：WO2004012726A3

  公开（公告）日：2004-06-03
• Insecticidal properties of some derivatives of L-canavanine
  作者：Gerald A. Rosenthal、D. L. Dahlman、Peter A. Crooks、Supinan Na Phuket、L. S. Trifonov

  DOI：10.1021/jf00058a034

  日期：1995.10

  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.
• [EN] COMBINATION THERAPY WITH INHIBITORS OF INDUCIBLE NITRIC OXIDE SYNTHASE AND ALKYLATING AGENTS<br/>[FR] THERAPIE DE COMBINAISON AVEC DES INHIBITEURS DE LA SYNTHASE DU MONOXYDE D'AZOTE INDUCTIBLE ET DES AGENTS D'ALKYLATION
  申请人：PHARMACIA CORP

  公开号：WO2005025620A3

  公开（公告）日：2007-01-11