1-acetamido-1-deoxy-5a-carba-β-D-lyxo-hex-5(5a)-enopyranose | 1169701-63-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-acetamido-1-deoxy-5a-carba-β-D-lyxo-hex-5(5a)-enopyranose
• CAS: 1169701-63-6
• 化学式: C₉H₁₅NO₅
• 分子量: 217.222
• InChiKey: UMECHVJCACFLQQ-BGZDPUMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.49
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  110.02
• 氢给体数：
  5.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-acetamido-1-deoxy-5a-carba-β-D-lyxo-hex-5(5a)-enopyranose 在 lithium hydroxide 、 水 作用下， 反应 26.5h， 以33%的产率得到1,2-bis-epi-valienamine
  参考文献：
  名称：

  β-Mannosidase and β-hexosaminidase inhibitors: synthesis of 1,2-bis-epi-valienamine and 1-epi-2-acetamido-2-deoxy-valienamine from d-mannose

  摘要：

  A partially protected C-5=C-5a unsaturated carbasugar with alpha-lyxo configuration is synthesised in five steps and 26% overall yield from a known mannose-derived hemiacetal, using ring-closing metathesis as a key step. This carbasugar is converted into valienamine derivatives with beta-lyxo (i.e., corresponding to beta-manno at C-1-C-4), alpha-lyxo (i.e., corresponding to alpha-manno at C-1-C-4) and beta-2-acetamido-2-deoxy-xylo (i.e., corresponding to beta-GlcNAc at C-1-C-4) configurations. This is the first report of the synthesis of the beta-lyxo compound, 1,2-bis-epi-valienamine, which was found to inhibit Cellulomonas fimi beta-mannosidase (CfMan2A) with K(i) 140 mu M. We report the crystal structures of three protected C-5=C-5a unsaturated carbasugars with lyxo configuration. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.016
• 作为产物：
  描述：

  3,4,6-tri-O-benzyl-1-deoxy-1-trichloroacetamido-5a-carba-β-D-lyxo-hex-5(5a)-enopyranose 在 氨 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 1.33h， 以40 mg的产率得到1-acetamido-1-deoxy-5a-carba-β-D-lyxo-hex-5(5a)-enopyranose
  参考文献：
  名称：

  β-Mannosidase and β-hexosaminidase inhibitors: synthesis of 1,2-bis-epi-valienamine and 1-epi-2-acetamido-2-deoxy-valienamine from d-mannose

  摘要：

  A partially protected C-5=C-5a unsaturated carbasugar with alpha-lyxo configuration is synthesised in five steps and 26% overall yield from a known mannose-derived hemiacetal, using ring-closing metathesis as a key step. This carbasugar is converted into valienamine derivatives with beta-lyxo (i.e., corresponding to beta-manno at C-1-C-4), alpha-lyxo (i.e., corresponding to alpha-manno at C-1-C-4) and beta-2-acetamido-2-deoxy-xylo (i.e., corresponding to beta-GlcNAc at C-1-C-4) configurations. This is the first report of the synthesis of the beta-lyxo compound, 1,2-bis-epi-valienamine, which was found to inhibit Cellulomonas fimi beta-mannosidase (CfMan2A) with K(i) 140 mu M. We report the crystal structures of three protected C-5=C-5a unsaturated carbasugars with lyxo configuration. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.016