methyl 2-acetamido-2,6-dideoxy-α-D-xylo-hexopyranosid-4-ulose | 1030024-07-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: methyl 2-acetamido-2,6-dideoxy-α-D-xylo-hexopyranosid-4-ulose
• 英文别名: N-[(2S,3R,4R,6R)-4-hydroxy-2-methoxy-6-methyl-5-oxooxan-3-yl]acetamide
• CAS: 1030024-07-7
• 化学式: C₉H₁₅NO₅
• 分子量: 217.222
• InChiKey: XBYIDBWYTPFOCK-YWUKIDGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl 2-acetamido-3-O-acetyl-2,6-dideoxy-α-D-xylo-hexopyranosid-4-ulose 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以72%的产率得到methyl 2-acetamido-2,6-dideoxy-α-D-xylo-hexopyranosid-4-ulose
  参考文献：
  名称：

  Synthesis of methyl 2-acetamido-2,6-dideoxy-α- and β-d-xylo-hexopyranosid-4-ulose, a keto sugar which misled the analytical chemists

  摘要：

  To understand the contradictory results on the structure of the lipopolysaccharide isolated from a Yersinia enterocolitica O:3, both anomers of methyl 2-acetamido-2,6-dideoxy-D-xylo-hexopyranosid-4-ulose were prepared. The key steps of the synthetic pathway were the selective acetylation of the methyl 2-acetamido-2,6-dideoxy-alpha,beta-D-glucopyranosides, the oxidation of the 4-position to form the keto-sugars, and deacetylation to provide the target compound. Surprisingly, the last step was accompanied by a disproportionation to give methyl 2-acetamido-2,6-dideoxy-alpha- and beta-D-glucopyranosides and N-(5-hydroxy-6-methyl-4-oxo-4H-pyran-3-yl)acetamide as side-products. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.02.001

文献信息

• Synthesis of methyl 2-acetamido-2,6-dideoxy-α- and β-d-xylo-hexopyranosid-4-ulose, a keto sugar which misled the analytical chemists
  作者：Sabine Borowski、Dirk Michalik、Helmut Reinke、Christian Vogel、Anna Hanuszkiewicz、Katarzyna A. Duda、Otto Holst

  DOI：10.1016/j.carres.2008.02.001

  日期：2008.5

  To understand the contradictory results on the structure of the lipopolysaccharide isolated from a Yersinia enterocolitica O:3, both anomers of methyl 2-acetamido-2,6-dideoxy-D-xylo-hexopyranosid-4-ulose were prepared. The key steps of the synthetic pathway were the selective acetylation of the methyl 2-acetamido-2,6-dideoxy-alpha,beta-D-glucopyranosides, the oxidation of the 4-position to form the keto-sugars, and deacetylation to provide the target compound. Surprisingly, the last step was accompanied by a disproportionation to give methyl 2-acetamido-2,6-dideoxy-alpha- and beta-D-glucopyranosides and N-(5-hydroxy-6-methyl-4-oxo-4H-pyran-3-yl)acetamide as side-products. (c) 2008 Elsevier Ltd. All rights reserved.