1,2,4-tri-O-acetyl-2-azido-2-deoxy-L-fucose | 115435-17-1

• 分子结构分类: 有机化合物
• 英文名称: 1,2,4-tri-O-acetyl-2-azido-2-deoxy-L-fucose
• 英文别名: 2-azido-2-deoxy-1,3,4-tri-O-acetyl-L-fucopyranose；1,3,4-tri-O-acetyl-2-azidodeoxy-α-L-fucose；1,3,4-Tri-O-acetyl-2-azido-2-deoxy-alpha-L-fucopyranose；[(2S,3R,4S,5S,6S)-4,6-diacetyloxy-5-azido-2-methyloxan-3-yl] acetate
• CAS: 115435-17-1
• 化学式: C₁₂H₁₇N₃O₇
• 分子量: 315.283
• InChiKey: JBUGOMFHZVGOMN-WWSHQCSISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.84
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  136.89
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1,2,4-tri-O-acetyl-2-azido-2-deoxy-L-fucose 在 甲醇 、 sodium methylate 、 1,2-双(二苯基膦)乙烷 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 N-acetyl-α-L-fucosamine
  参考文献：
  名称：

  Azidonitration of Di-O-acetyl-L-fucal: X-Ray Crystal Structures of Intermediate Azidodeoxysugars and of the Bacterial Aminosugar N-Acetyl-L-fucosamine

  摘要：

  The azidonitration of di-O-acetyl-L-fucal has previously been shown to be an efficient route to the bacterial aminosugar N-acetyl-L-fucosamine. Upon repeating this sequence, with updated versions of the glycal formation and amide installation steps, we have obtained X-ray crystal structures of several of the addition products, which are now reported along with the solid-state structure of N-acetyl-L-fucosamine itself.

  DOI：

  10.1080/07328303.2012.658125
• 作为产物：
  描述：

  D-Fucose 在 sodium dihydrogenphosphate 、 sodium azide 、 高氯酸 、 ammonium cerium (IV) nitrate 、 氢溴酸 、 乙酸酐 、 溶剂黄146 、 锌 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 8.5h， 生成 1,2,4-tri-O-acetyl-2-azido-2-deoxy-L-fucose
  参考文献：
  名称：

  Synthesis of Staphylococcus aureus Type 5 Trisaccharide Repeating Unit: Solving the Problem of Lactamization

  摘要：

  The chemical synthesis of an orthogonally protected trisaccharide derived from the polysaccharide of Staphylococcus aureus Type 5, which is an attractive candidate for the development of immunotherapies, is described. The challenging alpha-fucosylation and beta-mannosylation are addressed through the careful choice of protecting groups. Lactamization of a beta-D-ManpNAcA moiety during deprotection was avoided by a late stage oxidation approach. Versatility of the trisaccharide was demonstrated by its transformation into a spacer-containing repeating unit suitable for immunological investigations.

  DOI：

  10.1021/acs.orglett.5b00031

文献信息

• A Chemical Reporter Strategy to Probe Glycoprotein Fucosylation
  作者：David Rabuka、Sarah C. Hubbard、Scott T. Laughlin、Sulabha P. Argade、Carolyn R. Bertozzi

  DOI：10.1021/ja064619y

  日期：2006.9.1

  Fucosylated glycoproteins are involved in many cell-cell recognition events and are markers of embryonic and malignant tissue. Here we report a method for rapid profiling of fucosylated glycoproteins from human cells using 6-azido fucose as a metabolic label.
• Ludewig, Michael; Thiem, Joachim, European Journal of Organic Chemistry, 1998, # 6, p. 1189 - 1191
  作者：Ludewig, Michael、Thiem, Joachim

  DOI：——

  日期：——
• Preparative synthesis of 2-acetamido-2,6-dideoxy-L-galactose (N-acetyl-L-fucosamine)
  作者：Abul K.M. Anisuzzaman、Derek Horton

  DOI：10.1016/0008-6215(87)80258-6

  日期：1987.11