2-azido-1-O-nitro-3,4-di-O-acetyl-L-fucose | 188790-06-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azido-1-O-nitro-3,4-di-O-acetyl-L-fucose
• CAS: 188790-06-9
• 化学式: C₁₀H₁₄N₄O₈
• 分子量: 318.243
• InChiKey: BHDHWVFRBCKVRT-RSMLHNCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.48
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  162.96
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2-azido-1-O-nitro-3,4-di-O-acetyl-L-fucose 在 甲醇 、 sodium methylate 、 sodium acetate 、 溶剂黄146 、 1,2-双(二苯基膦)乙烷 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 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 、 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 7.5h， 生成 2-azido-1-O-nitro-3,4-di-O-acetyl-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 versatile approach to the synthesis of mannosamine glycosides
  作者：Catherine Alex、Satsawat Visansirikul、Alexei V. Demchenko

  DOI：10.1039/d0ob01640c

  日期：——

  H-bond-mediated aglycone delivery (HAD) pathway. A new practical method for the stereoselective synthesis of β-glycosides of mannosamine is reported. The presence of the O-picoloyl group at the C-3 position of a mannosamine donor can provide high or complete stereocontrol. The method was also utilized for the synthesis of a biologically relevant trisaccharide related to the capsular polysaccharide of Streptococcus

  位于远端的O-吡啶甲酰基保护基团可以通过 H 键介导的糖苷配基传递 (HAD) 途径影响糖基化的立体选择性。报道了一种立体选择性合成甘露糖胺β-糖苷的实用新方法。在甘露糖胺供体的 C-3 位置存在O-吡啶甲酰基可以提供高度或完全的立体控制。该方法还用于合成与肺炎链球菌血清型4的荚膜多糖相关的生物学相关三糖。本文还报道了一种用配备有3- O-苯甲酰基的甘露糖胺供体实现完全α-甘露糖立体选择性的方法。