N-chloroacetyl-β-D-glucopyranosylamine | 157062-75-4

• 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-glucopyranosylamine
• 英文别名: N-(β-D-glucopyranosyl)chloroacetamide；2-chloro-N-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]acetamide
• CAS: 157062-75-4
• 化学式: C₈H₁₄ClNO₆
• 分子量: 255.655
• InChiKey: KYUJZNBOUYNSAF-RHROMQPHSA-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-glucopyranosylamine 在 sodium azide 、 Na β-zeolite 作用下， 以 水 、 丙酮 为溶剂， 反应 32.0h， 生成 N-(2,3,4,6-tetra-O-acetylated-β-D-glucopyranosyl)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-glucopyranosylamine 、 氯乙酸酐 以 甲醇 为溶剂， 以65%的产率得到N-chloroacetyl-β-D-glucopyranosylamine
  参考文献：
  名称：

  Crystal Structures of β‐1‐N‐Chloroacetamido Derivatives of d‐Glucose and d‐Galactose

  摘要：

  Crystal structures of 1-N-(beta-D-glucopyranosyl)chloroacetamide (1), an inhibitor of glycogen phosphorylase, and the corresponding galactopyranosyl amide (2) have been determined. Both crystals belong to P2(1)2(1)2(1) space group with 1 having the unit cell dimensions of a=7.939(3), b=9.547(3) and c=14.157(2) Angstrom, while those of 2 are, a=7.636(10), b=9.004(8) and c=14.807(5) Angstrom. The sugar ring takes a C-4(1) conformation and the amide linkage exists in Z-anti conformation in both crystals. The torsion angle O5-C1-N1-C1' is -93.9(5) for 1 and -111.5(3)degrees for 2. The conformational preference of C1 and N1 in 1 and 2 is found to be between anti and gauche. The molecular assembly in both 1 and 2 is stabilized by a finite chain of hydrogen bonds starting from N1H and ending at O1', whereas a ten membered hydrogen-bonded ring involving O4H and O5 is observed in 1.

  DOI：

  10.1081/car-120026600

文献信息

• 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.
• [EN] TREATMENT OF DIABETES<br/>[FR] TRAITEMENT DU DIABETE
  申请人：UNIV NEWCASTLE

  公开号：WO2006043036A2

  公开（公告）日：2006-04-27

  [EN] The invention provides a composition comprising therapeutically effective amounts of a first agent adapted to promote glucokinase activation and a second agent adapted to inhibit or inactivate glycogen phosphorylase, and optionally a pharmaceutically acceptable vehicle. The composition may be used for the treatment of diabetes. The invention further provides methods of treating patients suffering from diabetes, and also a delivery system for use in a gene therapy of diabetes sufferers.
  [FR] L'invention concerne une composition comprenant des quantités efficaces thérapeutiquement d'un premier agent permettant de promouvoir une activation de la glucokinase et un second agent conçu pour inhiber ou inactiver la phosphorylase du glycogène, et éventuellement un véhicule pharamceutiquement acceptable. La composition peut être utilisée pour le traitement du diabète. L'invention concerne en particulier des procédés pour traiter des patients souffrant du diabète, et également un système d'administration destiné à être utilisé dans une thérapie génique conçue pour les personnes souffrant de diabète.
• 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.
• Crystal Structures of β‐1‐<i>N</i>‐Chloroacetamido Derivatives of <scp>d</scp>‐Glucose and <scp>d</scp>‐Galactose
  作者：Udayanath Aich、Thiruneelakantan Lakshmanan、Babu Varghese、Duraikkannu Loganathan

  DOI：10.1081/car-120026600

  日期：2003.12.31

  Crystal structures of 1-N-(beta-D-glucopyranosyl)chloroacetamide (1), an inhibitor of glycogen phosphorylase, and the corresponding galactopyranosyl amide (2) have been determined. Both crystals belong to P2(1)2(1)2(1) space group with 1 having the unit cell dimensions of a=7.939(3), b=9.547(3) and c=14.157(2) Angstrom, while those of 2 are, a=7.636(10), b=9.004(8) and c=14.807(5) Angstrom. The sugar ring takes a C-4(1) conformation and the amide linkage exists in Z-anti conformation in both crystals. The torsion angle O5-C1-N1-C1' is -93.9(5) for 1 and -111.5(3)degrees for 2. The conformational preference of C1 and N1 in 1 and 2 is found to be between anti and gauche. The molecular assembly in both 1 and 2 is stabilized by a finite chain of hydrogen bonds starting from N1H and ending at O1', whereas a ten membered hydrogen-bonded ring involving O4H and O5 is observed in 1.