N-chloroacetyl-β-D-mannopyranosylamine | 183583-60-0

• 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-mannopyranosylamine
• 英文别名: N-(β-D-mannopyranosyl)chloroacetamide；Mannosylchloroacetamide；2-chloro-N-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]acetamide
• CAS: 183583-60-0
• 化学式: C₈H₁₄ClNO₆
• 分子量: 255.655
• InChiKey: KYUJZNBOUYNSAF-NDBSEGGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 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-chloroacetyl-β-D-mannopyranosylamine 在 sodium azide 、 Na β-zeolite 作用下， 以 水 、 丙酮 为溶剂， 反应 34.0h， 生成 N-(2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl)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：

  1-氨基-1-脱氧-beta-D-吡喃甘露糖 、 氯乙酸酐 以 N,N-二甲基甲酰胺 为溶剂， 以63%的产率得到N-chloroacetyl-β-D-mannopyranosylamine
  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

• Glycoconjugates of amino acids. Preparation throughN-alkylation of amino acids withN-chloroacetyl-β-glycopyranosylamines
  作者：L. M. Likhosherstov、O. S. Novikova、V. N. Shibaev

  DOI：10.1007/bf02495306

  日期：1999.7

  Monoalkylation of amino acids of different structural types withN-chloroacetyl-glycosylamines was shown to be applicable for the preparation of glycoconjugates containing β-d-galactose,N-acetyl-β-d-glucosamine, β-d-mannose, and lactose residues. The glycoconjugates were synthesized from amino acids with secondary (sarcosine,l-proline) or primary (l-2- and 4-aminobutyric acids,l-tryptophan) amino groups

  不同结构类型的氨基酸与 N-氯乙酰-糖胺的单烷基化被证明适用于制备含有 β-d-半乳糖、N-乙酰-β-d-葡糖胺、β-d-甘露糖和乳糖残基的糖缀合物。糖缀合物由具有二级（肌氨酸，l-脯氨酸）或一级（l-2-和4-氨基丁酸，l-色氨酸）氨基的氨基酸以及各种氨基二羧酸（N-甲基-dl-天冬氨酸、dl-天冬氨酸、l-谷氨酸和dl-2-氨基己二酸）。获得的衍生物可能对本系列生理活性化合物的糖靶向作用感兴趣。
• N-glycyl-β-glycopyranosylamines, derivatives of mono- and disaccharides, and their use for the preparation of carboxylic acid glycoconjugates
  作者：L. M. Likhosherstov、O. S. Novikova、A. O. Zheltova、V. N. Shibaev

  DOI：10.1007/bf02495096

  日期：2000.8

  ofN-glycyl-β-glycopyranosylamines, derivatives of monosaccharides (d-galactose,d-mannose,l-fucose, andN-acetyl-d-glucosamine) and disaccharides (lactose, melibiose, cellobiose, and maltose). These compounds were demonstrated to be useful for the preparation of glycoconjugates of biologically active compounds containing the carboxy group (nicotinic, orotic, kynurenic, and indoleacetic acids). Synthetic pathways

  为合成 N-甘氨酰-β-吡喃葡萄糖胺、单糖衍生物（d-半乳糖、d-甘露糖、l-岩藻糖和 N-乙酰-d-葡糖胺）和二糖（乳糖、蜜二糖、纤维二糖、和麦芽糖）。这些化合物被证明可用于制备含有羧基的生物活性化合物（烟碱酸、乳清酸、犬尿酸和吲哚乙酸）的糖缀合物。开发了使用丙二酸和l-酒石酸衍生物将N-甘氨酰-β-吡喃葡萄糖胺转化为含有羧基的衍生物的合成途径。
• Glycoconjugates of amines: alkylation of primary and secondary amines withN-chloroacetyl-β-glycopyranosylamines
  作者：L. M. Likhosherstov、O. S. Novikova、V. N. Shibaev

  DOI：10.1007/bf02503499

  日期：1998.6

  Efficient monoalkylation of a series of primary and secondary amines was demonstrated with the use ofN-chloroacetylglycosylamines derived fromd-glucose,d-galactose,d-mannose,N-acetyl-d-glucosamine, and lactose. The reaction was shown to be useful for incorporation of carbohydrate residues into physiologically active compounds. Glycoconjugates of some derivatives of piperazine, 2-phenylethylamine, tryptamine

  使用衍生自 d-葡萄糖、d-半乳糖、d-甘露糖、N-乙酰基-d-葡糖胺和乳糖的 N-氯乙酰基糖胺证明了一系列伯胺和仲胺的有效单烷基化。该反应被证明可用于将碳水化合物残基结合到生理活性化合物中。制备了哌嗪、2-苯乙胺、色胺和重要生物胺（去甲麻黄碱、章鱼胺、多巴胺）的一些衍生物的糖缀合物。
• 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.