Methyl 3-azido-6-bromo-2,3,6-trideoxy-α-D-arabino-hexopyranoside | 98383-20-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 3-azido-6-bromo-2,3,6-trideoxy-α-D-arabino-hexopyranoside
• 英文别名: (2S,3S,4R,6S)-4-azido-2-(bromomethyl)-6-methoxyoxan-3-ol
• CAS: 98383-20-1
• 化学式: C₇H₁₂BrN₃O₃
• 分子量: 266.095
• InChiKey: DLCQRKWNUQWNLT-JWXFUTCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  53
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 3-azido-6-bromo-2,3,6-trideoxy-α-D-arabino-hexopyranoside 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以73%的产率得到methyl α-D-acosaminide
  参考文献：
  名称：

  Rationale for the synthesis and preliminary biological evaluation of highly active new antitumor nitrosoureido sugars

  摘要：

  Various new nitrosoureido derivatives of di- or trideoxy sugars were synthesized. The influence of the hydroxyl substitution pattern, the configuration at the anomeric center, and the absolute configuration of the sugar moiety on the antitumor activity of a series of nitrosoureido derivatives of di- and trideoxy sugars was studied. All compounds showed a very significant activity in vivo against L1210 leukemia, B16 melanocarcinoma, and Lewis lung carcinoma. Methyl 3-[3-(2-chloroethyl)-3-nitrosoureido]-2,3-dideoxy-alpha-D-arabino- hexopyranoside, 24 (NSC 609224), was found to be the most active compound. When treated with 24 (NSC 609224) at 20 mg/kg on day 1, at least 90% of the L1210 leukemia and B16 melanocarcinoma bearing mice showed a survival of over 60 days for a LD50 value for this compound of 42 mg/kg.

  DOI：

  10.1021/jm00121a005
• 作为产物：
  描述：

  methyl 3-azido-4-O-benzoyl-6-bromo-2,3,6-trideoxy-α-D-arabino-hexopyranoside 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以95%的产率得到Methyl 3-azido-6-bromo-2,3,6-trideoxy-α-D-arabino-hexopyranoside
  参考文献：
  名称：

  Rationale for the synthesis and preliminary biological evaluation of highly active new antitumor nitrosoureido sugars

  摘要：

  Various new nitrosoureido derivatives of di- or trideoxy sugars were synthesized. The influence of the hydroxyl substitution pattern, the configuration at the anomeric center, and the absolute configuration of the sugar moiety on the antitumor activity of a series of nitrosoureido derivatives of di- and trideoxy sugars was studied. All compounds showed a very significant activity in vivo against L1210 leukemia, B16 melanocarcinoma, and Lewis lung carcinoma. Methyl 3-[3-(2-chloroethyl)-3-nitrosoureido]-2,3-dideoxy-alpha-D-arabino- hexopyranoside, 24 (NSC 609224), was found to be the most active compound. When treated with 24 (NSC 609224) at 20 mg/kg on day 1, at least 90% of the L1210 leukemia and B16 melanocarcinoma bearing mice showed a survival of over 60 days for a LD50 value for this compound of 42 mg/kg.

  DOI：

  10.1021/jm00121a005

文献信息

• Synthesis of New Pseudodisaccharide Aminoglycoside Antibiotics from Carbohydrates.
  作者：ISTVÁN F. PELYVÁS、MÁRIA MÁDI-PUSKÁS、ZOLTÁN G. TÓTH、ZSOLT VARGA、MIKLÓS HORNYÁK、GYULA BATTA、FERENC SZTARICSKAI

  DOI：10.7164/antibiotics.48.683

  日期：——

  Novel pseudodisaccharide-type aminocyclitol antibiotic models, built up from D-arabinose, D-ribose, D-glucosamine, L-ristosamine and L-acosamine have been synthesized by the glycosylation of. suitably protected (azido)deoxyinosose aglycones derived by the Ferrier carbocyclic ring transformation of carbohydrate precursors. An alternative approach to related pseudodisaccharides, based on the Ferrier carbocyclization of reducing disaccharides, has also been elaborated. This latter method extends the scope of the Ferrier reaction, by demonstrating that acid-labile 2-deoxydisaccharides can also be readily transformed into the corresponding pseudodisaccharides under the slightly acidic conditions of this ring-transformation.

  通过糖基化反应，合成了由D-阿拉伯糖、D-核糖、D-葡糖胺、L-里斯托糖胺和L-阿科糖胺构成的新型pseudo二糖型氨基环醇抗生素模型。这些合成过程利用了从碳水化合物前体通过费里尔碳环变换得到的适当保护的(叠氮)去氧肌醇苷元。基于费里尔碳环化的还原二糖的另一种相关pseudo二糖合成方法也得到了详细阐述。这种方法通过展示在稍微酸性条件下，不稳定的2-脱氧二糖也能容易地转化为相应的pseudo二糖，从而扩展了费里尔反应的应用范围。
• Rationale for the synthesis and preliminary biological evaluation of highly active new antitumor nitrosoureido sugars
  作者：Pierre Roger、Claude Monneret、Jean Paul Fournier、Patrick Choay、Roselyne Gagnet、Charles Gosse、Yves Letourneux、Ghanem Atassi、Alain Gouyette

  DOI：10.1021/jm00121a005

  日期：1989.1

  Various new nitrosoureido derivatives of di- or trideoxy sugars were synthesized. The influence of the hydroxyl substitution pattern, the configuration at the anomeric center, and the absolute configuration of the sugar moiety on the antitumor activity of a series of nitrosoureido derivatives of di- and trideoxy sugars was studied. All compounds showed a very significant activity in vivo against L1210 leukemia, B16 melanocarcinoma, and Lewis lung carcinoma. Methyl 3-[3-(2-chloroethyl)-3-nitrosoureido]-2,3-dideoxy-alpha-D-arabino- hexopyranoside, 24 (NSC 609224), was found to be the most active compound. When treated with 24 (NSC 609224) at 20 mg/kg on day 1, at least 90% of the L1210 leukemia and B16 melanocarcinoma bearing mice showed a survival of over 60 days for a LD50 value for this compound of 42 mg/kg.