N-(9-fluorenylmethoxycarbonyl)-O-[2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl]-L-threonine allyl ester | 868259-93-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-(9-fluorenylmethoxycarbonyl)-O-[2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl]-L-threonine allyl ester
• CAS: 868259-93-2
• 化学式: C₄₄H₄₆N₂O₁₀
• 分子量: 762.857
• InChiKey: OFGBHXBXUHKWOG-VOIBRNFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.96
• 重原子数：
  56.0
• 可旋转键数：
  14.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  139.88
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  N-(9-fluorenylmethoxycarbonyl)-O-[2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl]-L-threonine allyl ester 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以83%的产率得到N-(9-fluorenylmethoxycarbonyl)-O-[2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl]-L-threonine
  参考文献：
  名称：

  Chemical Synthesis of 23 kDa Glycoprotein by Repetitive Segment Condensation:  A Synthesis of MUC2 Basal Motif Carrying Multiple O-GalNAc Moieties

  摘要：

  Peptide thioester corresponding to a MUC2 tandem repeat unit, which retains seven GaINAc moieties, was prepared by the Fmoc method followed by the low TfOH treatment to remove benzyl groups at the carbohydrate portions. The glycosylated peptide thioester was then consecutively joined by the activation of a thioester group by silver ions to obtain a MUC2 tandem repeat model composed of 141 amino acids with 42 GaINAc moieties.

  DOI：

  10.1021/ja053711b
• 作为产物：
  描述：

  N-(9-fluorenylmethoxycarbonyl)-O-[2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl]-L-threonine allyl ester 在 溶剂黄146 、 锌 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 N-(9-fluorenylmethoxycarbonyl)-O-[2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl]-L-threonine allyl ester
  参考文献：
  名称：

  Chemical Synthesis of 23 kDa Glycoprotein by Repetitive Segment Condensation:  A Synthesis of MUC2 Basal Motif Carrying Multiple O-GalNAc Moieties

  摘要：

  Peptide thioester corresponding to a MUC2 tandem repeat unit, which retains seven GaINAc moieties, was prepared by the Fmoc method followed by the low TfOH treatment to remove benzyl groups at the carbohydrate portions. The glycosylated peptide thioester was then consecutively joined by the activation of a thioester group by silver ions to obtain a MUC2 tandem repeat model composed of 141 amino acids with 42 GaINAc moieties.

  DOI：

  10.1021/ja053711b