2-acetamido-3,6-anhydro-2-deoxy-α-D-gulofuranose | 545439-98-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: 2-acetamido-3,6-anhydro-2-deoxy-α-D-gulofuranose
• 英文别名: N-[(3R,3aS,5S,6R,6aS)-3,5-dihydroxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl]acetamide
• CAS: 545439-98-3
• 化学式: C₈H₁₃NO₅
• 分子量: 203.195
• InChiKey: VAHGSMNMJYMZLN-HEIBUPTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.03
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  88.02
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  beta-D-半乳糖基-(1→3)-N-乙酰基-D-半乳糖胺 生成 口服葡萄糖 、 2-acetamido-2,3-dideoxy-β-D-threohex-2-enofuranose 、 2-acetamido-2,3-dideoxy-α-D-threohex-2-enofuranose 、 2-acetamido-3,6-anhydro-2-deoxy-β-D-idofuranose 、 2-acetamido-3,6-anhydro-2-deoxy-α-D-idofuranose 、 2-acetamido-3,6-anhydro-2-deoxy-β-D-gulofuranose 、 2-acetamido-3,6-anhydro-2-deoxy-α-D-gulofuranose
  参考文献：
  名称：

  Thermal decomposition of β-d-galactopyranosyl-(1→3)-2-acetamido-2-deoxy-d-hexopyranoses under neutral conditions

  摘要：

  beta-D-Galactopyranosyl-(1 -> 3)-2-acetamido-2-deoxy-D-glucose (LNB) and beta-D-galactopyranosyl-(1 -> 3)-2-acetamido-2-deoxy-D-galactose (GNB) decompose rapidly upon heating into D-galactose and mono-dehydrated derivatives of the corresponding 2-acetamido-2-deoxy-D-hexoses, including 2-acetamido-2,3-dideoxy-hex-2-enofuranoses and bicyclic 2-acetamido-3,6-anhydro-2-deoxy-hexofuranoses. The decomposition is conducted under neutral conditions where glycosyl linkages are generally believed to be stable. The half-lives of LNB and GNB were 8.1 min and 20 min, respectively, at 90 degrees C and pH 7.5. The pH dependency of decomposition rates suggests that the instabilities are an extension of the conditions for the peeling reaction, often observed with glycans of O-linked glycoproteins under alkaline conditions. Such decomposition under the neutral conditions is commonly observed with 3-O-linked reducing aldoses. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.06.003