1,6-anhydro-4-azido-2,4-dideoxy-β-D-arabino-hexopyranose | 270088-65-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 1,6-anhydro-4-azido-2,4-dideoxy-β-D-arabino-hexopyranose
• 英文别名: (1S,2S,3R,5R)-2-azido-6,8-dioxabicyclo[3.2.1]octan-3-ol
• CAS: 270088-65-8
• 化学式: C₆H₉N₃O₃
• 分子量: 171.156
• InChiKey: CKMSKMZLSPUPIU-KAZBKCHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• 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：

  1,6-anhydro-4-azido-2,4-dideoxy-β-D-arabino-hexopyranose 在 Amberlite R₁₅ (H)+ 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-(2-chloroethyl)-3-[(2S,3S,4R,6S)-4-hydroxy-2-(hydroxymethyl)-6-methoxyoxan-3-yl]-1-nitrosourea
  参考文献：
  名称：

  Synthesis and antitumour activity of a new series of nitrosoureido sugars

  摘要：

  New nitrosoureido derivatives of di- or tri-deoxy-sugars have been synthesized. Very potent antitumour activity against L1210 leukaemia was exhibited by the compounds derived from methyl 3-amino-3,4-dideoxy-beta- and alpha- and 4-amino-2,4-dideoxy-beta- and alpha-D-arabino-hexopyranosides; 24, 26, 28 and 29, respectively. in further evaluation against B16 melanocarcinoma bearing mice, only compounds 24 and 26 displayed significant activity. Owing to its lower acute toxicity, methyl 3-[3-(2-chloroethyl)-3-nitrosoureido]-3,4dideoxy-beta-D-arabino-hexopyranoside 24 appeared as the best candidate for preclinical studies. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00114-8
• 作为产物：
  描述：

  1,6-脱水-2-脱氧-2-碘-D-吡喃葡萄糖 在 palladium on activated charcoal 吡啶 、 sodium azide 、 氢气 、 sodium methylate 、 氯化铵 、 三乙胺 作用下， 以 甲醇 、 氯仿 、 水 、 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 90.0h， 生成 1,6-anhydro-4-azido-2,4-dideoxy-β-D-arabino-hexopyranose
  参考文献：
  名称：

  Synthesis and antitumour activity of a new series of nitrosoureido sugars

  摘要：

  New nitrosoureido derivatives of di- or tri-deoxy-sugars have been synthesized. Very potent antitumour activity against L1210 leukaemia was exhibited by the compounds derived from methyl 3-amino-3,4-dideoxy-beta- and alpha- and 4-amino-2,4-dideoxy-beta- and alpha-D-arabino-hexopyranosides; 24, 26, 28 and 29, respectively. in further evaluation against B16 melanocarcinoma bearing mice, only compounds 24 and 26 displayed significant activity. Owing to its lower acute toxicity, methyl 3-[3-(2-chloroethyl)-3-nitrosoureido]-3,4dideoxy-beta-D-arabino-hexopyranoside 24 appeared as the best candidate for preclinical studies. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00114-8

文献信息

• Synthesis of 1,6-Anhydro-2,3,4-trideoxy-2,3-epimino- and 1,6-Anhydro-2,3,4-trideoxy-3,4-epimino-β-D-hexopyranoses and Their NMR and Infrared Spectra
  作者：Jindřich Karban、Miloš Buděšínský、Jiří Kroutil

  DOI：10.1135/cccc20041939

  日期：——

  A complete series of 2,3,4-trideoxy-2,3-epimino and 2,3,4-trideoxy-3,4-epimino derivatives of 1,6-anhydro-β-D-hexopyranoses were prepared by lithium aluminium hydride reduction of vicinal trans azido tosylates. Unusual formation of the aziridine ring from precursors with the trans-diequatorial arrangement of the reacting groups was observed. NMR and infrared spectra of the aziridines are discussed.

  通过锂铝氢还原相邻的trans偶氮基对甲苯磺酸酯，制备了一系列1,6-脱水-β-D-己糖苷的2,3,4-三去氧-2,3-表胺和2,3,4-三去氧-3,4-表胺衍生物。观察到从反应基团的trans-二赤道排列的前体中形成环氮丙烷的不寻常现象。讨论了环氮丙烷的NMR和红外光谱。
• Synthesis and antitumour activity of a new series of nitrosoureido sugars
  作者：C Monneret

  DOI：10.1016/s0223-5234(00)00114-8

  日期：2000.1

  New nitrosoureido derivatives of di- or tri-deoxy-sugars have been synthesized. Very potent antitumour activity against L1210 leukaemia was exhibited by the compounds derived from methyl 3-amino-3,4-dideoxy-beta- and alpha- and 4-amino-2,4-dideoxy-beta- and alpha-D-arabino-hexopyranosides; 24, 26, 28 and 29, respectively. in further evaluation against B16 melanocarcinoma bearing mice, only compounds 24 and 26 displayed significant activity. Owing to its lower acute toxicity, methyl 3-[3-(2-chloroethyl)-3-nitrosoureido]-3,4dideoxy-beta-D-arabino-hexopyranoside 24 appeared as the best candidate for preclinical studies. (C) 2000 Editions scientifiques et medicales Elsevier SAS.