prop-2-enyl (2S)-4-[[(2R,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoate | 1054660-84-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: prop-2-enyl (2S)-4-[[(2R,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoate
• CAS: 1054660-84-2
• 化学式: C₃₈H₄₈N₄O₁₅
• 分子量: 800.817
• InChiKey: DOUALVOAVQCBOM-HJXKMJLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  57
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  281
• 氢给体数：
  9
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  prop-2-enyl (2S)-4-[[(2R,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoate 在 吡啶 、 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 苯硅烷 作用下， 以 二氯甲烷 为溶剂， 生成 N⁴-[2-acetamido-2-deoxy-4-O-(2-acetamido-2-deoxy-3,4,6-tri-O-tert-butyldimethylsilyl-β-D-glucopyranosyl)-3,6-di-O-tert-butyldimethylsilyl-β-D-glucopyranosyl]-N²-(fluoren-9-ylmethyloxycarbonyl)-L-aspartic acid
  参考文献：
  名称：

  立体选择性合成β-连接的TBDMS保护的壳二糖-天冬酰胺：淀粉样蛋白生成糖肽的通用构建基块

  摘要：

  描述了一种对β-连接的碳水化合物具有选择性的Fmoc-1-Asn [β-壳二糖（TBDMS）5 ] -OH的简单有效的合成方法。在代表小鼠病毒蛋白（PrPGP）的175-195 †片段的糖基化淀粉样蛋白生成肽的合成中说明了此构件的实用性。

  DOI：

  10.1016/s0040-4039(01)01524-6
• 作为产物：
  描述：

  N,N'-Diacetylchitobiose 在 ammonium carbamate 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 prop-2-enyl (2S)-4-[[(2R,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoate
  参考文献：
  名称：

  Improving Glycopeptide Synthesis:  A Convenient Protocol for the Preparation of β-Glycosylamines and the Synthesis of Glycopeptides

  摘要：

  Herein we apply a recently introduced protocol using ammonium carbamate in methanol to the amination of crude chitobiose leading to 1,beta-aminochitobiose. This simple, one-step procedure allows a facile preparation of unstable glycosylamines in contrast to the commonly implemented ammonium bicarbonate based amination of water-soluble carbohydrates. The new amination protocol leads to an improved synthesis of the key chitobiosyl-asparagine building block for the SPPS of glycopeptides. The utility of the method is demonstrated with the synthesis of a 39-amino acid glycoprotein.

  DOI：

  10.1021/jo047801v

文献信息

• Stereoselective synthesis of β-linked TBDMS-protected chitobiose-asparagine: a versatile building block for amyloidogenic glycopeptides
  作者：Carlos J Bosques、Vincent W.-F Tai、Barbara Imperiali

  DOI：10.1016/s0040-4039(01)01524-6

  日期：2001.10

  A simple and efficient synthesis of a Fmoc-l-Asn[β-chitobiose(TBDMS)5]-OH with selectivity for the β-linked carbohydrate is described. The utility of this building block is illustrated in the synthesis of a glycosylated amyloidogenic peptide representing the 175-195† fragment of the mouse prion protein (PrPGP).

  描述了一种对β-连接的碳水化合物具有选择性的Fmoc-1-Asn [β-壳二糖（TBDMS）5 ] -OH的简单有效的合成方法。在代表小鼠病毒蛋白（PrPGP）的175-195 †片段的糖基化淀粉样蛋白生成肽的合成中说明了此构件的实用性。
• Improving Glycopeptide Synthesis:  A Convenient Protocol for the Preparation of β-Glycosylamines and the Synthesis of Glycopeptides
  作者：Christian P. R. Hackenberger、Mary K. O'Reill、Barbara Imperiali

  DOI：10.1021/jo047801v

  日期：2005.4.1

  Herein we apply a recently introduced protocol using ammonium carbamate in methanol to the amination of crude chitobiose leading to 1,beta-aminochitobiose. This simple, one-step procedure allows a facile preparation of unstable glycosylamines in contrast to the commonly implemented ammonium bicarbonate based amination of water-soluble carbohydrates. The new amination protocol leads to an improved synthesis of the key chitobiosyl-asparagine building block for the SPPS of glycopeptides. The utility of the method is demonstrated with the synthesis of a 39-amino acid glycoprotein.