4-O-(β-D-galactopyranosyl)-N-chloroacetyl-β-D-glucopyranosylamine | 183583-61-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-(β-D-galactopyranosyl)-N-chloroacetyl-β-D-glucopyranosylamine
• 英文别名: N-chloroacetyl-4-O-(β-D-galactopyranosyl)-β-D-glucopyranosylamine；N-chloroacetyl-beta-lactosylamine；2-chloro-N-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]acetamide
• CAS: 183583-61-1
• 化学式: C₁₄H₂₄ClNO₁₁
• 分子量: 417.798
• InChiKey: VAHNUSGQYVKGOM-YBMXKUSISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.1
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  198
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  4-O-(β-D-galactopyranosyl)-N-chloroacetyl-β-D-glucopyranosylamine 在 ammonium hydroxide 作用下， 反应 40.0h， 以70%的产率得到N-glycyl-β-lactosylamine
  参考文献：
  名称：

  N-glycyl-β-glycopyranosylamines，单糖和二糖的衍生物，以及它们在制备羧酸糖缀合物中的用途

  摘要：

  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。

  DOI：

  10.1007/bf02495096
• 作为产物：
  描述：

  β-lactosylamine 、 氯乙酸酐 以 N,N-二甲基甲酰胺 为溶剂， 以70%的产率得到4-O-(β-D-galactopyranosyl)-N-chloroacetyl-β-D-glucopyranosylamine
  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 of spacered derivatives of β-lactosylamine with an amino function at the terminal position of an aglycon
  作者：L. M. Likhosherstov、O. S. Novikova、L. O. Kononov、V. N. Shibaev

  DOI：10.1007/s11172-006-0409-6

  日期：2006.7

  A set of N-acyllactosylamine derivatives containing a terminal amino group in aglycons of various lengths (up to 16 atoms) and various hydrophilicities were synthesized. The aglycons were represented by di-, tri-, and pentapeptides containing glycine and serine residues and by aglycons containing fragments of tartaric acid or a tertiary amine.

  合成了一组包含末端氨基的N-酰基乳糖胺衍生物，这些衍生物的非糖部分长度各异（最长可达16个原子）且亲水性各异。非糖部分由含有甘氨酸和丝氨酸残基的二肽、三肽和五肽构成，以及包含酒石酸或三级胺片段的非糖部分。
• 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 of bi- and tervalent ligands of galectins, derivatives of β-lactosylamine, with the amino group in the terminal position of the spacer
  作者：L. M. Likhosherstov、O. S. Novikova、G. V. Mokrov

  DOI：10.1007/s11172-008-0104-x

  日期：2008.3

  A method for the synthesis of glycoclusters by N-alkylation of N-glycyl-β-lactosylamine with N-chloroacetyl derivatives of β-lactosylamine and N,N’-iminodiacetyldilactosylamine has been developed. The glycoclusters obtained with two and three lactosylamine residues with the amino group in the spacer were found to be suitable for further conjugation with carboxy-containing physiologically active compounds.

  通过 N-甘氨酰-β-乳糖基胺与 β-乳糖基胺和 N,N'-亚氨基二乙酰基二乳糖基胺的 N-氯乙酰衍生物的 N-烷基化合成聚糖的方法已经开发出来。研究发现，带有两个和三个乳糖基胺残基的聚糖簇，其中间的氨基基团适合与含羧基的生理活性化合物进一步共轭。
• 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。
• 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.