1-(3-azido-3-deoxy-β-D-glucopyranosyl)-thymine | 1389345-13-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3-azido-3-deoxy-β-D-glucopyranosyl)-thymine
• 英文别名: 1-[(2R,3R,4S,5S,6R)-4-azido-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 1389345-13-4
• 化学式: C₁₁H₁₅N₅O₆
• 分子量: 313.27
• InChiKey: YTBCBDOWRVVCFL-MGPZHUSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-(3-azido-3-deoxy-β-D-glucopyranosyl)-thymine 在 palladium on activated charcoal 、 氢气 、 三乙胺 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 24.0h， 以72%的产率得到1-(3-Amino-3-desoxy-β-D-glucopyranosyl)-thymin
  参考文献：
  名称：

  Stereocontrolled Facile Synthesis and Biological Evaluation of (3′S) and (3′R)-3′-Amino (and Azido)-3′-Deoxy Pyranonucleosides

  摘要：

  This article describes the synthesis of (3'S) and (3'R)-3'-amino-3'-deoxy pyranonucleosides and their precursors (3'S) and (3'R)-3'-azido-3'-deoxy pyranonucleosides. Azidation of 1,2:5,6-di-O-isopropylidene-3-O-toluenesulfonyl-alpha-D-allofuranose followed by hydrolysis and subsequent acetylation afforded 3-azido-3-deoxy-1,2,4,6-tetra-O-acetyl-D-glucopyranose, which upon coupling with the proper silylated bases, deacetylation, and catalytic hydrogenation, obtained the target 3'-amino-3'-deoxy-beta-D-glucopyranonucleosides. The desired 1-(3'-amino-3'-deoxy-beta-D-allopyranosyl) 5-fluorouracil was readily prepared from the suitable imidazylate sugar after azidation followed by a protection/deprotection sequence and reduction of the unprotected azido precursor. No antiviral activity was observed for the novel nucleosides. Moderate cytostatic activity was recorded for the 5-fluorouracil derivatives.

  DOI：

  10.1080/15257770.2012.696759
• 作为产物：
  描述：

  3-azido-3-deoxy-1,2:5,6-di-(O-isopropylidene)-α-D-glucofuranose 在 氨 、 六甲基二硅氮烷 、 糖精 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 3.5h， 生成 1-(3-azido-3-deoxy-β-D-glucopyranosyl)-thymine
  参考文献：
  名称：

  Stereocontrolled Facile Synthesis and Biological Evaluation of (3′S) and (3′R)-3′-Amino (and Azido)-3′-Deoxy Pyranonucleosides

  摘要：

  This article describes the synthesis of (3'S) and (3'R)-3'-amino-3'-deoxy pyranonucleosides and their precursors (3'S) and (3'R)-3'-azido-3'-deoxy pyranonucleosides. Azidation of 1,2:5,6-di-O-isopropylidene-3-O-toluenesulfonyl-alpha-D-allofuranose followed by hydrolysis and subsequent acetylation afforded 3-azido-3-deoxy-1,2,4,6-tetra-O-acetyl-D-glucopyranose, which upon coupling with the proper silylated bases, deacetylation, and catalytic hydrogenation, obtained the target 3'-amino-3'-deoxy-beta-D-glucopyranonucleosides. The desired 1-(3'-amino-3'-deoxy-beta-D-allopyranosyl) 5-fluorouracil was readily prepared from the suitable imidazylate sugar after azidation followed by a protection/deprotection sequence and reduction of the unprotected azido precursor. No antiviral activity was observed for the novel nucleosides. Moderate cytostatic activity was recorded for the 5-fluorouracil derivatives.

  DOI：

  10.1080/15257770.2012.696759

文献信息

• Stereocontrolled Facile Synthesis and Biological Evaluation of (3′<i>S</i>) and (3′<i>R</i>)-3′-Amino (and Azido)-3′-Deoxy Pyranonucleosides
  作者：Stella Manta、Vanessa Parmenopoulou、Christos Kiritsis、Athina Dimopoulou、Nikolaos Kollatos、Ioannis Papasotiriou、Jan Balzarini、Dimitri Komiotis

  DOI：10.1080/15257770.2012.696759

  日期：2012.7

  This article describes the synthesis of (3'S) and (3'R)-3'-amino-3'-deoxy pyranonucleosides and their precursors (3'S) and (3'R)-3'-azido-3'-deoxy pyranonucleosides. Azidation of 1,2:5,6-di-O-isopropylidene-3-O-toluenesulfonyl-alpha-D-allofuranose followed by hydrolysis and subsequent acetylation afforded 3-azido-3-deoxy-1,2,4,6-tetra-O-acetyl-D-glucopyranose, which upon coupling with the proper silylated bases, deacetylation, and catalytic hydrogenation, obtained the target 3'-amino-3'-deoxy-beta-D-glucopyranonucleosides. The desired 1-(3'-amino-3'-deoxy-beta-D-allopyranosyl) 5-fluorouracil was readily prepared from the suitable imidazylate sugar after azidation followed by a protection/deprotection sequence and reduction of the unprotected azido precursor. No antiviral activity was observed for the novel nucleosides. Moderate cytostatic activity was recorded for the 5-fluorouracil derivatives.