methyl 3-azido-4,6-O-benzylidene-2,3-dideoxy-α-D-arabino-hexopyranoside | 6386-19-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 3-azido-4,6-O-benzylidene-2,3-dideoxy-α-D-arabino-hexopyranoside
• 英文别名: 3-Azido-4,6-O-benzyliden-2,3-didesoxy-methyl-α-D-arabino-hexapyranosid；(4aR,6S,8R,8aS)-8-azido-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 6386-19-2
• 化学式: C₁₄H₁₇N₃O₄
• 分子量: 291.307
• InChiKey: QPIUTUWBOILDRM-JABUTEAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.54
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  85.68
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 3-azido-4,6-O-benzylidene-2,3-dideoxy-α-D-arabino-hexopyranoside 在 palladium on activated charcoal 甲醇 、 氢气 、 乙酰氯 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 生成 methyl 3-amino-2,3-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

文献信息

• Synthetic studies on optically active .BETA.-lactams. Stereocontrolled synthesis of chiral thienamycin intermediate from D-glucose.
  作者：Nobuo Ikota、Osamu Yoshino、Kenji Koga

  DOI：10.1248/cpb.30.1929

  日期：——

  Chiral thienamycin intermediate (12) having the correct absolute configuration was synthesized from D-glucose.

  以 D-葡萄糖为原料合成了具有正确绝对构型的手性硫霉素中间体 (12)。