N-chloroacetyl-β-D-xylopyranosylamine | 183583-62-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-chloroacetyl-β-D-xylopyranosylamine
• 英文别名: 2-chloro-N-[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]acetamide
• CAS: 183583-62-2
• 化学式: C₇H₁₂ClNO₅
• 分子量: 225.629
• InChiKey: AUGHBCJRMWPPMT-VYNVVFCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 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：
  99
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-chloroacetyl-β-D-xylopyranosylamine 在 sodium azide 、 Na β-zeolite 、 sodium methylate 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 32.25h， 生成 N-(β-D-xylopyranosyl)azidoacetamide
  参考文献：
  名称：

  Synthesis ofN‐(β‐Glycopyrano‐syl)azidoacetamides

  摘要：

  N-(beta-Glycopyranosyl)azidoacetamides, mimetics of the widely distributed GlcNAc-Asn linkage in glycoproteins, have been synthesized in good yields starting from beta-glycopyranosylamines in four steps involving selective N-chloroacetylation, peracetylation catalyzed by Na beta-zeolite, displacement of the Cl group by NaN3 in aqueous acetone, and Zemplen de-O-acetylation.

  DOI：

  10.1081/car-200049402
• 作为产物：
  描述：

  D-吡喃木糖 在 氨 、 碳酸氢铵 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 N-chloroacetyl-β-D-xylopyranosylamine
  参考文献：
  名称：

  Synthesis ofN-chioroacetyl-?-glycopyranosylamines, derivatives of monosaccharides and lactose

  摘要：

  N-Chloroacetyl-beta-glycosylamines were synthesized from various monosaccharides (hexoses, pentoses, deoxysugars, uronic acids, and sugar phosphates) and a disaccharide (lactose) by N-acylation of the corresponding beta-glycosylamines with chloroacetic anhydride in DMF. In some cases, treatment of monosaccharides with NH3 in the presence of (NH4)CO3 in MeOH or aqueous MeOH was more efficient than the methods previously described, as it gave beta-glycosylamines in higher yields.

  DOI：

  10.1007/bf01431821

文献信息

• Synthesis ofN-chioroacetyl-?-glycopyranosylamines, derivatives of monosaccharides and lactose
  作者：L. M. Likhosherstov、O. S. Novikova、V. N. Shibaev、N. K. Kochetkov

  DOI：10.1007/bf01431821

  日期：1996.7

  N-Chloroacetyl-beta-glycosylamines were synthesized from various monosaccharides (hexoses, pentoses, deoxysugars, uronic acids, and sugar phosphates) and a disaccharide (lactose) by N-acylation of the corresponding beta-glycosylamines with chloroacetic anhydride in DMF. In some cases, treatment of monosaccharides with NH3 in the presence of (NH4)CO3 in MeOH or aqueous MeOH was more efficient than the methods previously described, as it gave beta-glycosylamines in higher yields.
• Synthesis of<i>N</i>‐(β‐Glycopyrano‐syl)azidoacetamides
  作者：Udayanath Aich、Duraikkannu Loganathan

  DOI：10.1081/car-200049402

  日期：2005.1

  N-(beta-Glycopyranosyl)azidoacetamides, mimetics of the widely distributed GlcNAc-Asn linkage in glycoproteins, have been synthesized in good yields starting from beta-glycopyranosylamines in four steps involving selective N-chloroacetylation, peracetylation catalyzed by Na beta-zeolite, displacement of the Cl group by NaN3 in aqueous acetone, and Zemplen de-O-acetylation.