benzyl N-(benzyloxycarbonyl)-D,L-allothreoninate | 85995-51-3

• 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 N-(benzyloxycarbonyl)-D,L-allothreoninate
• 英文别名: N-benzyloxycarbonyl-DL-allothreonine benzyl ester；N-Benzyloxycarbonyl-DL-allothreonin-benzylester；benzyl (2R,3R)-3-hydroxy-2-(phenylmethoxycarbonylamino)butanoate
• CAS: 85995-51-3
• 化学式: C₁₉H₂₁NO₅
• 分子量: 343.379
• InChiKey: VBKUVUJWFDXTMS-RHSMWYFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 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：

  benzyl N-(benzyloxycarbonyl)-D,L-allothreoninate 在 三氟化硼乙醚 、 氢溴酸 、 溶剂黄146 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (S)-2-Benzyloxycarbonylamino-5-[(R)-1-((1R,2S)-1-benzyloxycarbonyl-2-methoxy-propylcarbamoyl)-2-benzylsulfanyl-ethylcarbamoyl]-pentanoic acid benzyl ester
  参考文献：
  名称：

  Synthesis of δ-(l-α-aminoadipoyl)-l-cysteinyl-d-(O-methyl)-d-allothreonine a substrate for isopenicillin-N synthase and its O-methyl-d-threonine epimer

  摘要：

  The paper describes the synthesis of two epimeric tripeptides delta-(L-alpha-aminoadipoyl)-L-cysteinyl-D-(O-methyl)-D-threonine (13) and 6-(L-alpha-aminoadipoyl)-L-cysteinyl-D-(O-methyl)-D-allothreonine (14), modified substrates for the isopenicillin-N synthase enzyme. The D-allothreonine tripeptide (14)has been shown to be an excellent substrate for the enzyme whereas the D-threonine epimer did not react at all. The compound formed by the enzyme with the D-allothreonine tripeptide is a new 2-alpha-methoxypenicillin. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00280-4
• 作为产物：
  描述：

  二氮杂甲苯 在 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 0.5h， 生成 benzyl N-(benzyloxycarbonyl)-D,L-allothreoninate
  参考文献：
  名称：

  Synthesis of δ-(l-α-aminoadipoyl)-l-cysteinyl-d-(O-methyl)-d-allothreonine a substrate for isopenicillin-N synthase and its O-methyl-d-threonine epimer

  摘要：

  The paper describes the synthesis of two epimeric tripeptides delta-(L-alpha-aminoadipoyl)-L-cysteinyl-D-(O-methyl)-D-threonine (13) and 6-(L-alpha-aminoadipoyl)-L-cysteinyl-D-(O-methyl)-D-allothreonine (14), modified substrates for the isopenicillin-N synthase enzyme. The D-allothreonine tripeptide (14)has been shown to be an excellent substrate for the enzyme whereas the D-threonine epimer did not react at all. The compound formed by the enzyme with the D-allothreonine tripeptide is a new 2-alpha-methoxypenicillin. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00280-4

文献信息

• Carbon-13 NMR spectroscopy, a useful tool to determine the enantiomeric purity of synthetic threonine-containing glycopeptides. Spectra of diastereoisomeric .alpha.- and .beta.-D-galactopyranosyl-L- and D-threonine and -L- and -D-allothreonine
  作者：A. A. Pavia、J. M. Lacombe

  DOI：10.1021/jo00163a028

  日期：1983.7
• O-(Substituted)-α-amino-β-hydroxybutyric Acids
  作者：DONALD L. ROSS、CHARLES G. SKINNER、WILLIAM SHIVE

  DOI：10.1021/jo01092a014

  日期：1959.10
• Synthesis of δ-(l-α-aminoadipoyl)-l-cysteinyl-d-(O-methyl)-d-allothreonine a substrate for isopenicillin-N synthase and its O-methyl-d-threonine epimer
  作者：Sigthór Pétursson、Jack E Baldwin

  DOI：10.1016/s0040-4020(98)00280-4

  日期：1998.5

  The paper describes the synthesis of two epimeric tripeptides delta-(L-alpha-aminoadipoyl)-L-cysteinyl-D-(O-methyl)-D-threonine (13) and 6-(L-alpha-aminoadipoyl)-L-cysteinyl-D-(O-methyl)-D-allothreonine (14), modified substrates for the isopenicillin-N synthase enzyme. The D-allothreonine tripeptide (14)has been shown to be an excellent substrate for the enzyme whereas the D-threonine epimer did not react at all. The compound formed by the enzyme with the D-allothreonine tripeptide is a new 2-alpha-methoxypenicillin. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.