3,6-anhydro-5-azido-5-deoxy-1,2-O-isopropylidene-β-L-ido-furanose | 95443-67-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: 3,6-anhydro-5-azido-5-deoxy-1,2-O-isopropylidene-β-L-ido-furanose
• 英文别名: 3,6-anhydro-5-azido-5-deoxy-1,2-O-isopropylidene-β-L-idofuranose；(1S,2R,6R,8R,9S)-9-azido-4,4-dimethyl-3,5,7,11-tetraoxatricyclo[6.3.0.02,6]undecane
• CAS: 95443-67-7
• 化学式: C₉H₁₃N₃O₄
• 分子量: 227.22
• InChiKey: UXBBHYUBSGNJHP-BZCSJUTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  51.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,6-anhydro-5-azido-5-deoxy-1,2-O-isopropylidene-β-L-ido-furanose 在 吡啶 、 硫酸氢铵 、 溶剂黄146 、 六甲基二硅氮烷 作用下， 以 水 、 甲苯 为溶剂， 反应 30.5h， 生成 1-(2-O-acetyl-3,6-anhydro-5-azido-5-deoxy-β-D-glucofuranosyl)-2,6-dichloropurine
  参考文献：
  名称：

  Synthesis and biological evaluation of 2,6-dichloropurine bicyclonucleosides containing a triazolyl-carbohydrate moiety

  摘要：

  A series of bicyclic nucleosides containing a triazolyl-carbohydrate moiety were synthesized and their antitumor activity in vitro for human cancer cell lines was also tested. Compound 11 was synthesized efficiently with 3,6-anhydro sugar 7 as raw material, while compound 7 was prepared from 1,2; 5,6-di-O-isopropylidene-alpha-D-glucose. Compounds 12a-e were synthesized by treating compound 11 with alkynes, catalyzed by copper(I). After removal of the acetyl protecting groups, the target compounds 5a-e showed significant inhibitory activity against EC109, PC-3, MGC-803, and HGC-7 cell lines. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.10.004
• 作为产物：
  描述：

  3,6-anhydro-1,2-O-isopropylidene-5-O-toluene-p-sulfonyl-α-D-glucofuranose 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以79%的产率得到3,6-anhydro-5-azido-5-deoxy-1,2-O-isopropylidene-β-L-ido-furanose
  参考文献：
  名称：

  Stereoselective Synthesis and Biological Studies of the C2 and C3 Epimer and the Enantiomer of Pachastrissamine (Jaspine B)

  摘要：

  据报道，研究人员从 d-葡萄糖中合成了天麻素 B 的 C2 和 C3 外比体以及对映体。这些异构体以及雅司平 B 及其 C2 表亚体对 MCF7 细胞的细胞毒性与市售抗癌药物表柔比星相关。

  DOI：

  10.1055/s-0029-1217096

文献信息

• First example of 5/6-O-linked pseudosaccharides: synthesis of bicyclic nucleosides containing azido or extended carbohydrate moiety
  作者：Joy Krishna Maity、Subhranshu Mukherjee、Michael G.B. Drew、Basudeb Achari、Sukhendu B. Mandal

  DOI：10.1016/j.carres.2007.08.013

  日期：2007.12

  the 5,6-ether linked pseudodisaccharide 3, and pseudotrisaccharide 4. However, reaction of 1 with sodium ethoxide in ethanol afforded 2 as the sole product, elaborated to the bicyclic azidonucleosides 9 and 16. Acetylated bicyclic nucleosides 17-19 with extended carbohydrate residues have been synthesized from 3.

  用氢化钠在四氢呋喃中处理衍生自d-葡萄糖的底物1提供3,6-脱水单糖2以及5,6-醚连接的假二糖3和假三糖4。但是，1与乙醇钠在乙醇中的反应提供了作为单独产物的2，其被详述为双环叠氮核苷9和16。具有延长的碳水化合物残基的乙酰化双环核苷17-19已经由3合成。