N-formyl-β-D-glucopyranosylamine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-formyl-β-D-glucopyranosylamine
• 英文别名: glucosyl formamide；Rzbdtnmwsazkkr-xuuwzhrgsa-；N-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]formamide
• 化学式: C₇H₁₃NO₆
• 分子量: 207.183
• InChiKey: RZBDTNMWSAZKKR-XUUWZHRGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  119
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-formyl-β-D-glucopyranosylamine 在 吡啶 、 三光气 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成 (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-isocyanotetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  Synthesis of β-Glycosyl Formamides Through N-Glycosylation of Unprotected Carbohydrates

  摘要：

  Two new synthetic routes involving N-glycosylation of unprotected carbohydrates were developed for the preparation of beta-glycosyl formamides. Using this protocol, D-glucose, D-xylose, D-galactose and D-maltose were transformed to their corresponding beta-glycosyl formamides.

  DOI：

  10.3987/com-16-13584
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-1-deoxy-1-formamido-beta-d-glucopyranose 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以64%的产率得到N-formyl-β-D-glucopyranosylamine
  参考文献：
  名称：

  The structure of glycosyl amides: A combined study by NMR spectroscopy, X-ray crystallography, and computational chemistry

  摘要：

  The structure of N-formyl, N-acetyl-N-methyl, and N-acetyl glycosylamines has been studied by NMR spectroscopy in solution, single crystal X-ray diffractometry, and corroborated by PM3 semiempirical calculations. The results quite agree with an anti conformation around the glycosydic bond for these substances. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10321-0

文献信息

• Synthesis of β-Glycosyl Formamides Through N-Glycosylation of Unprotected Carbohydrates
  作者：Yoshiyasu Ichikawa、Akihito Matsukawa、Yumiko Tomita、Rika Mimura、Ayumi Kitamori、Hiyoshizo Kotsuki、Toshiya Masuda、Mitsutoshi Maeda、Keiji Nakano

  DOI：10.3987/com-16-13584

  日期：——

  Two new synthetic routes involving N-glycosylation of unprotected carbohydrates were developed for the preparation of beta-glycosyl formamides. Using this protocol, D-glucose, D-xylose, D-galactose and D-maltose were transformed to their corresponding beta-glycosyl formamides.
• The structure of glycosyl amides: A combined study by NMR spectroscopy, X-ray crystallography, and computational chemistry
  作者：Martín Avalos、Reyes Babiano、María J. Carretero、Pedro Cintas、Francisco J. Higes、JoséL. Jiménez、Juan C. Palacios

  DOI：10.1016/s0040-4020(97)10321-0

  日期：1998.1

  The structure of N-formyl, N-acetyl-N-methyl, and N-acetyl glycosylamines has been studied by NMR spectroscopy in solution, single crystal X-ray diffractometry, and corroborated by PM3 semiempirical calculations. The results quite agree with an anti conformation around the glycosydic bond for these substances. (C) 1997 Elsevier Science Ltd. All rights reserved.