5'-amino-2',3',-di-O-benzyl-5'-deoxyuridine | 262286-59-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: 5'-amino-2',3',-di-O-benzyl-5'-deoxyuridine
• 英文别名: 1-[(2R,3R,4R,5R)-5-(aminomethyl)-3,4-bis(phenylmethoxy)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 262286-59-9
• 化学式: C₂₃H₂₅N₃O₅
• 分子量: 423.469
• InChiKey: FDKOJHTUJBEJKS-ZHHKINOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5'-amino-2',3',-di-O-benzyl-5'-deoxyuridine 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 68.0h， 生成 4-((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-N-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl]-butyramide
  参考文献：
  名称：

  合成2-（N-乙酰氨基）-2-脱氧-C-吡喃葡萄糖基核苷作为几丁质合酶的潜在抑制剂。

  摘要：

  含有N-乙酰基氨基葡萄糖氨基和尿苷单元的C-吡喃葡萄糖基核苷（1-4）已被合成为UDP-GlcNAc的不可水解底物类似物，目的是抑制几丁质合酶。关键中间体4-（2'-（N-乙酰氨基）-3'，4'，6'-三-O-苄基-2'-脱氧-α-D-吡喃葡萄糖基）丁-2-烯酸（5 ）是由全苄基化（N-乙酰氨基）-α-C-烯丙基葡糖苷（7）通过连续的氧化裂解，Wittig烯化和酯脱保护制备的。酸5与尿苷衍生物（6a或6b）的羟基或胺官能团偶合，分别得到酯12和酰胺14。用能更好地实现酯12或酰胺14中共轭双键的二羟基化。四氧化物/氯酸钡，得到两种非对映异构体混合物的预期二醇13和15。化合物12-15催化氢化后，得到所需的化合物1-4。

  DOI：

  10.1021/jo991206p
• 作为产物：
  描述：

  2',3'-Di-O-Benzyl-uridin 在 1,3-丙二硫醇 、 sodium tetrahydroborate 、 sodium azide 、 四溴化碳 、 三乙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 17.0h， 生成 5'-amino-2',3',-di-O-benzyl-5'-deoxyuridine
  参考文献：
  名称：

  合成2-（N-乙酰氨基）-2-脱氧-C-吡喃葡萄糖基核苷作为几丁质合酶的潜在抑制剂。

  摘要：

  含有N-乙酰基氨基葡萄糖氨基和尿苷单元的C-吡喃葡萄糖基核苷（1-4）已被合成为UDP-GlcNAc的不可水解底物类似物，目的是抑制几丁质合酶。关键中间体4-（2'-（N-乙酰氨基）-3'，4'，6'-三-O-苄基-2'-脱氧-α-D-吡喃葡萄糖基）丁-2-烯酸（5 ）是由全苄基化（N-乙酰氨基）-α-C-烯丙基葡糖苷（7）通过连续的氧化裂解，Wittig烯化和酯脱保护制备的。酸5与尿苷衍生物（6a或6b）的羟基或胺官能团偶合，分别得到酯12和酰胺14。用能更好地实现酯12或酰胺14中共轭双键的二羟基化。四氧化物/氯酸钡，得到两种非对映异构体混合物的预期二醇13和15。化合物12-15催化氢化后，得到所需的化合物1-4。

  DOI：

  10.1021/jo991206p

文献信息

• Synthesis of Sugar Azido or Amino Esters and Their Use as Building Blocks for the Preparation of Saccharide Nucleosides
  作者：Juan Xie

  DOI：10.1002/1099-0690(200210)2002:20<3411::aid-ejoc3411>3.0.co;2-q

  日期：2002.10

  selective removal of the primary benzyl group or selective acetolysis of the primary benzyl group of β-C-glycoside as key steps. Such structures have been successfully used as scaffolds for the synthesis of novel saccharide nucleosides. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

  已经通过 TMSOTf/Ac2O 介导的 α-C-糖基化制备了几种带有 α- 或 β-CD-吡喃葡萄糖基主链的糖叠氮基或氨基酯，同时选择性去除初级苄基或选择性乙酰化初级苄基β-C-糖苷作为关键步骤。此类结构已成功用作合成新型糖核苷的支架。(© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)
• Synthesis and evaluation of a C-glycosyl nucleoside as an inhibitor of chitin synthase
  作者：Juan Xie、Annie Thellend、Hubert Becker、Anne Vidal-Cros

  DOI：10.1016/s0008-6215(01)00191-4

  日期：2001.8

  As part of our ongoing program devoted to inhibit chitin synthases, we have prepared a novel C-glycosyl nucleoside as metabolically stable substrate analog of UDP-GlcNAc. The synthetic strategy relies on the consecutive coupling of nucleoside and amino C-glycosyl moieties with L-tartaric acid. However, this compound inhibited only weakly chitin synthase I, with an IC(50) value of 20 mM.

  作为我们正在进行的旨在抑制几丁质合酶的计划的一部分，我们已经制备了一种新的C-糖基核苷作为UDP-GlcNAc的代谢稳定底物类似物。合成策略依赖于核苷和氨基C-糖基部分与L-酒石酸的连续偶联。但是，该化合物仅抑制弱几丁质合酶I，IC（50）值为20 mM。
• Synthesis of sugar–amino acid–nucleosides as potential glycosyltransferase inhibitors
  作者：Kannan Vembaiyan、Jean A. Pearcey、Milan Bhasin、Todd L. Lowary、Wei Zou

  DOI：10.1016/j.bmc.2010.11.044

  日期：2011.1

  Sugar-amino acid-nucleosides (SAAN) were synthesized to mimic glycosyl nucleotide donors based on the hypothesis that a basic amino acid may interact with carboxylate groups of the enzyme in a manner similar to the diphosphate metal ion complex. C-Glycoside analogues of the D-galactopyranose or L-arabinofuranose ring systems, and four amino acids (lysine, glutamine, tryptophan, and histidine), were chosen for this study. The targets were synthesized and tested against GlfT2, a galactofuranosyltransferase essential for cell wall galactan biosynthesis in Mycobacterium tuberculosis. The inhibition assay showed that analogues containing histidine and tryptophan are moderate inhibitors of GlfT2. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.
• Synthesis of iminoalditol analogues of galactofuranosides and their activities against glycosidases
  作者：Mahendra Sandbhor、Milan Bhasin、Dean T. Williams、Margaret Hsieh、Shih-Hsiung Wu、Wei Zou

  DOI：10.1016/j.carres.2008.07.013

  日期：2008.11

  Iminoalditol analogues of galactofuranosides were synthesized from 1-C-(2'-oxo-propyl)-1,4-dideoxy1,4-imino-D-galactosides and different amines by reductive amination. followed by removal of protecting groups. The activity of these compounds against galactosidases and other glycosidases was investigated. The best inhibitor against beta-galactosidase (bovine liver) is a diastereomeric mixture of an iminoalditol (10h), which contains a hydrophobic hexadecyl aglycon (R=C16H33), whereas no significant inhibitory activity was observed with compounds having a hydrophilic aglycon. Surprisingly, activation of alpha-galactosidase (coffee bean) by 10th was also observed. Because these results were obtained from a mixture of iminoalditols, the inhibition and activation of glycosidases could result from different diastereomers. Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.
• Synthesis of 2-(<i>N</i>-Acetylamino)-2-deoxy-<i>C</i>-glucopyranosyl Nucleosides as Potential Inhibitors of Chitin Synthases
  作者：Jérôme Grugier、Juan Xie、Isabelle Duarte、Jean-Marc Valéry

  DOI：10.1021/jo991206p

  日期：2000.2.1

  derivatives (6a or 6b) afforded, respectively, the ester 12 and amide 14. The dihydroxylation of the conjugated double bond in ester 12 or amide 14 was better achieved with osmium tetraoxide/barium chlorate, leading to the expected diols 13 and 15 as a mixture of two diastereoisomers. The desired compounds 1-4 were obtained after catalytic hydrogenation of compounds 12-15.

  含有N-乙酰基氨基葡萄糖氨基和尿苷单元的C-吡喃葡萄糖基核苷（1-4）已被合成为UDP-GlcNAc的不可水解底物类似物，目的是抑制几丁质合酶。关键中间体4-（2'-（N-乙酰氨基）-3'，4'，6'-三-O-苄基-2'-脱氧-α-D-吡喃葡萄糖基）丁-2-烯酸（5 ）是由全苄基化（N-乙酰氨基）-α-C-烯丙基葡糖苷（7）通过连续的氧化裂解，Wittig烯化和酯脱保护制备的。酸5与尿苷衍生物（6a或6b）的羟基或胺官能团偶合，分别得到酯12和酰胺14。用能更好地实现酯12或酰胺14中共轭双键的二羟基化。四氧化物/氯酸钡，得到两种非对映异构体混合物的预期二醇13和15。化合物12-15催化氢化后，得到所需的化合物1-4。