2-acetamido-3,6-anhydro-2-deoxy-D-glucofuranose

• 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-D-glucofuranose
• 英文别名: 2-acetamido-3,6-anhydro-2-deoxy-D-glucofurnose；N-[(3R,3aR,6R,6aR)-3,5-dihydroxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl]acetamide
• 化学式: C₈H₁₃NO₅
• 分子量: 203.195
• InChiKey: VAHGSMNMJYMZLN-RTRLPJTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  88
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-acetamido-3,6-anhydro-2-deoxy-D-glucofuranose 、 异戊酰氯 在 吡啶 作用下， 反应 2.0h， 生成 2-acetamido-3,6-anhydro-2-deoxy-5-O-isovaleryl-α-D-glucofuranose 、 2-acetamido-3,6-anhydro-2-deoxy-5-O-isovaleryl-β-D-glucofuranose
  参考文献：
  名称：

  Novel and facile synthesis of furanodictines A and B based on transformation of 2-acetamido-2-deoxy-d-glucose into 3,6-anhydro hexofuranoses

  摘要：

  A novel synthesis of furanodictines A[2-acetamido-3,6-anhydro-2-deoxy-5-O-isovaleryl-D-glucofuranose (1)] and B [2-acetamido-3,6-anhydro-2-deoxy-5-O-isovaleryl-D-mannofuranose (2)] is described starting from 2-acetamido-2-deoxy-D-glucose (G1cNAc). The synthetic protocol is based on deriving the epimeric bicyclic 3,6-anhydro sugars [2-acetamido-3,6-anhydro-2-deoxy-D-glucofuranose (4) and 2-acetamido-3,6-anhydro-2-deoxy-D-mannofuranose (5)] from GlcNAc. Reaction with borate upon heating led to a facile transformation of GlcNAc into the desired epimeric 3,6-anhydro sugars. The C5 hydroxyl group of the 3,6-anhydro compounds 4 and 5 was regioselectively esterified with the isovaleryl chloride to complete the synthesis of furanodictines A and B, respectively. The targets 1 and 2 were synthesized in only two steps requiring no protection/deprotection. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.10.007

文献信息

• Novel and facile synthesis of furanodictines A and B based on transformation of 2-acetamido-2-deoxy-d-glucose into 3,6-anhydro hexofuranoses
  作者：Makoto Ogata、Takeshi Hattori、Ryota Takeuchi、Taichi Usui

  DOI：10.1016/j.carres.2009.10.007

  日期：2010.1

  A novel synthesis of furanodictines A[2-acetamido-3,6-anhydro-2-deoxy-5-O-isovaleryl-D-glucofuranose (1)] and B [2-acetamido-3,6-anhydro-2-deoxy-5-O-isovaleryl-D-mannofuranose (2)] is described starting from 2-acetamido-2-deoxy-D-glucose (G1cNAc). The synthetic protocol is based on deriving the epimeric bicyclic 3,6-anhydro sugars [2-acetamido-3,6-anhydro-2-deoxy-D-glucofuranose (4) and 2-acetamido-3,6-anhydro-2-deoxy-D-mannofuranose (5)] from GlcNAc. Reaction with borate upon heating led to a facile transformation of GlcNAc into the desired epimeric 3,6-anhydro sugars. The C5 hydroxyl group of the 3,6-anhydro compounds 4 and 5 was regioselectively esterified with the isovaleryl chloride to complete the synthesis of furanodictines A and B, respectively. The targets 1 and 2 were synthesized in only two steps requiring no protection/deprotection. (C) 2009 Elsevier Ltd. All rights reserved.