N-(benzyloxycarbonyl)-L-alanyl-L-threonyl-L-alanine benzyl ester | 86961-60-6

• 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: N-(benzyloxycarbonyl)-L-alanyl-L-threonyl-L-alanine benzyl ester
• 英文别名: Cbz-Ala-Thr-Ala-OBn；benzyl (2S)-2-[[(2S,3R)-3-hydroxy-2-[[(2S)-2-(phenylmethoxycarbonylamino)propanoyl]amino]butanoyl]amino]propanoate
• CAS: 86961-60-6
• 化学式: C₂₅H₃₁N₃O₇
• 分子量: 485.537
• InChiKey: VXOWNNRCASHUGB-UGNRZPKXSA-N

物化性质

• 熔点：
  173 °C
• 沸点：
  750.4±60.0 °C(Predicted)
• 密度：
  1.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  143
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(benzyloxycarbonyl)-L-alanyl-L-threonyl-L-alanine benzyl ester 在 吡啶 、 4 A molecular sieve 、 camphor-10-sulfonic acid 、 silver perchlorate 、 三甲基铵三氧化硫共聚物 、 tin(ll) chloride 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 166.0h， 生成 (S)-2-[(2S,3R)-3-((2S,3R,4R,5R,6R)-3-Acetylamino-4-benzyloxy-5-hydroxy-6-sulfooxymethyl-tetrahydro-pyran-2-yloxy)-2-((S)-2-benzyloxycarbonylamino-propionylamino)-butyrylamino]-propionic acid benzyl ester
  参考文献：
  名称：

  Sequential Glycoproteins:  Practical Method for the Synthesis of Antifreeze Glycoprotein Models Containing Base Labile Groups

  摘要：

  Practical and versatile methods for the preparation of glycopeptide polymers containing base labile moieties were established by use of 1-isobuthoxycarbonyl-2-isobuthoxy-1,2-dihydroquinoline (IIDQ) or 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) as polycondensation agents of glycopeptide units without any protection on the carbohydrate residues. These methods were applied for the synthesis of mucin-like glycoprotein mimics related to antifreeze glycoproteins (AFGPs), giving the target O-acetylated glycopolypeptides efficiently, while the conventional DPPA (diphenylphosphoryl azide) method gave complex mixtures of acyl migrated compounds.

  DOI：

  10.1021/ma049756z
• 作为产物：
  描述：

  Boc-L-Thr-L-Ala-OBn 在 盐酸 、 二苯基膦叠氮化物 、 三乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 N-(benzyloxycarbonyl)-L-alanyl-L-threonyl-L-alanine benzyl ester
  参考文献：
  名称：

  Efficient and versatile synthesis of mucin-like glycoprotein mimics

  摘要：

  An efficient synthetic method of sequential glycopeptide-polymer by means of the combined chemical and enzymatic strategy was applied to the practical synthesis of some tandem repeating mucin-type glycoproteins. Versatility of the present synthetic strategy was demonstrated by elucidating some physicochemical and conformational analyses of these synthetic mucins. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01359-5

文献信息

• Efficient and versatile synthesis of mucin-like glycoprotein mimics
  作者：Yuki Tachibana、Naoki Matsubara、Fumio Nakajima、Tetsuro Tsuda、Sakae Tsuda、Kenji Monde、Shin-Ichiro Nishimura

  DOI：10.1016/s0040-4020(02)01359-5

  日期：2002.12

  An efficient synthetic method of sequential glycopeptide-polymer by means of the combined chemical and enzymatic strategy was applied to the practical synthesis of some tandem repeating mucin-type glycoproteins. Versatility of the present synthetic strategy was demonstrated by elucidating some physicochemical and conformational analyses of these synthetic mucins. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Sequential Glycoproteins:  Practical Method for the Synthesis of Antifreeze Glycoprotein Models Containing Base Labile Groups
  作者：Yuki Tachibana、Kenji Monde、Shin-Ichiro Nishimura

  DOI：10.1021/ma049756z

  日期：2004.9.1

  Practical and versatile methods for the preparation of glycopeptide polymers containing base labile moieties were established by use of 1-isobuthoxycarbonyl-2-isobuthoxy-1,2-dihydroquinoline (IIDQ) or 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) as polycondensation agents of glycopeptide units without any protection on the carbohydrate residues. These methods were applied for the synthesis of mucin-like glycoprotein mimics related to antifreeze glycoproteins (AFGPs), giving the target O-acetylated glycopolypeptides efficiently, while the conventional DPPA (diphenylphosphoryl azide) method gave complex mixtures of acyl migrated compounds.