3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactose | 138688-74-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactose
• CAS: 138688-74-1
• 化学式: C₁₅H₁₇N₃O₆
• 分子量: 335.316
• InChiKey: RYDFRWQLMDUANH-JEWKUQAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.43
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  122.98
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  phenyl 3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-1-seleno-α-D-galactopyranoside 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactose 、 3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactose
  参考文献：
  名称：

  Synthesis of the trisaccharide outer core fragment of Burkholderia cepacia pv. vietnamiensis lipooligosaccharide

  摘要：

  The synthesis of beta-Gal-(1 -> 3)-alpha-GalNAc-(1 -> 3)-beta-GalNAc allyl trisaccharide as the outer core fragment of Burkholderia cepacia pv. vietnamiensis lipooligosaccharide was accomplished through a concise, optimized, multi-step synthesis, having as key steps three glycosylations, that were in-depth studied performing them under several conditions. The target trisaccharide was designed with an allyl aglycone in order to open a future access to the conjugation with an immunogenic protein en route to the development of a synthetic neoglycoconjugate vaccine against this Burkholderia pathogen. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.12.007

文献信息

• Efficient Synthesis of Azido Sugars Using Fluorosulfuryl Azide Diazotransfer Reagent**
  作者：Joshua M. Kofsky、Gour C. Daskhan、Matthew S. Macauley、Chantelle J. Capicciotti

  DOI：10.1002/ejoc.202200108

  日期：2022.8.5

  An operationally simple protocol for diazotransfer on amine-containing carbohydrates has been developed. This high-yielding reaction can be conducted under ambient conditions. Reaction completion is indicated by the colour change of the Cu(II) catalyst. The utility of this protocol in chemical glycosylation has been demonstrated through the preparation of azide-containing glycosyl donors with orthogonal

  已开发出一种操作简单的含胺碳水化合物重氮转移方案。这种高产反应可以在环境条件下进行。反应完成由 Cu(II) 催化剂的颜色变化指示。该协议在化学糖基化中的效用已通过制备具有正交保护基团的含叠氮化物糖基供体得到证明。