ethyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thio-β-D-glucopyranoside | 183239-07-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6S)-3,4-diacetyloxy-5-azido-6-ethylsulfanyloxan-2-yl]methyl acetate
• CAS: 183239-07-8
• 化学式: C₁₄H₂₁N₃O₇S
• 分子量: 375.403
• InChiKey: IMXKEJXTNCXKBL-KSTCHIGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  128
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  ethyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thio-β-D-glucopyranoside 在 2,4,6-三甲基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 水 、 溴 、 silver trifluoromethanesulfonate 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-D-galactopyranosyl trichloroacetimidate
  参考文献：
  名称：

  一锅合成具有抗幽门螺杆菌抗生素活性的五糖。

  摘要：

  已经通过一锅两步糖基化策略合成了含有α-1,4-GlcNAc粘蛋白核心两支O聚糖的五糖。由于合成的五糖会抑制胆固醇α-葡萄糖基转移酶（IC50为0.47 mM），因此这种特殊的碳水化合物基序可提供针对幽门螺杆菌诱导的病理的保护作用。

  DOI：

  10.1039/b618662a
• 作为产物：
  描述：

  乙酸酐 、 ethyl 2-azido-2-deoxy-1-thio-β-D-glucopyranoside 以 吡啶 为溶剂， 反应 1.0h， 以92%的产率得到ethyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Oligosaccharide Structures from the Lipopolysaccharide of Moraxella catarrhalis

  摘要：

  The synthesis of the octasaccharide [p-(trifluoroacetamido)phenyl]ethyl 4-O-[2-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-beta-D-glucopyranosyl]-6-O-[2-O-[4-O-(4-O-alpha-D-galactopyranosyl-beta-D-galactopyranosyl)-alpha-D-glucopyranosyl]-beta-D-glucopyranosyl]-3-O-beta-D-glucopyranosyl-alpha-D-glucopyranoside, representing the outer part of the lipooligosaccharide from Moraxella catarrhalis serotype A, is described, together with a hepta-, a hexa-, and a pentasaccaride, composing parts thereof with shorter oligosaccharide chains substituted in the g-position of the central 3,4,6-branched glucose moiety. The versatility of the use of thioglycosides in oligosaccharide synthesis is shown, since throughout the synthesis thioglycosides are used as glycosyl donor precursors, either directly in dimethyl(methylthio)sulfonium triflate (DMTST)-promoted coupling reactions or after conversion to the corresponding glycosyl bromide in silver triflate-promoted couplings. The effects of different protecting groups, anomeric leaving groups, and solvents used in the various coupling reactions are often substantial, which necessitates the use of easily convertible intermediates.

  DOI：

  10.1021/jo960789p