methyl 3-O-acetyl-6-azido-4-O-benzoyl-2,6-dideoxy-α-D-arabino-hexopyranoside | 98383-29-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-acetyl-6-azido-4-O-benzoyl-2,6-dideoxy-α-D-arabino-hexopyranoside
• 英文别名: [(2R,3S,4R,6S)-4-acetyloxy-2-(azidomethyl)-6-methoxyoxan-3-yl] benzoate
• CAS: 98383-29-0
• 化学式: C₁₆H₁₉N₃O₆
• 分子量: 349.343
• InChiKey: MGDNBYGFLXQSHR-KBXIAJHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  85.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 3-O-acetyl-6-azido-4-O-benzoyl-2,6-dideoxy-α-D-arabino-hexopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以98%的产率得到methyl 6-azido-2,6-dideoxy-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
• 作为产物：
  描述：

  [(6S,8S,8aR)-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] acetate 生成 methyl 3-O-acetyl-6-azido-4-O-benzoyl-2,6-dideoxy-α-D-arabino-hexopyranoside
  参考文献：
  名称：

  CHOAY, P.;MONNERET, C.;ROGER, P.

  摘要：

  DOI：