[(2R,3S,4S,5R)-2-azido-5-(2,4-dioxopyrimidin-1-yl)-4-methyl-3-(2-methylpropanoyloxy)oxolan-2-yl]methyl 2-methylpropanoate | 1373391-44-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: [(2R,3S,4S,5R)-2-azido-5-(2,4-dioxopyrimidin-1-yl)-4-methyl-3-(2-methylpropanoyloxy)oxolan-2-yl]methyl 2-methylpropanoate
• CAS: 1373391-44-6
• 化学式: C₁₈H₂₅N₅O₇
• 分子量: 423.426
• InChiKey: RHYIHFIDODETBT-XJQUKVTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  126
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4S,5R)-2-azido-5-(2,4-dioxopyrimidin-1-yl)-4-methyl-3-(2-methylpropanoyloxy)oxolan-2-yl]methyl 2-methylpropanoate 在 甲醇 、 sodium methylate 作用下， 反应 0.5h， 以82%的产率得到sodium;1-[(2R,3S,4S,5R)-5-azido-4-hydroxy-5-(hydroxymethyl)-3-methyloxolan-2-yl]pyrimidin-3-ide-2,4-dione
  参考文献：
  名称：

  Synthesis of (4′R)-Azido-(2′R)-2′-Deoxy-2′-C-Methyluridine and Its Esters by Direct Iodide Displacement

  摘要：

  The synthesis of an anti-infective nucleoside intermediate was accomplished through direct iodine displacement at C-5' by a tetrabutylammonium carboxylate. This approach constitutes a more efficient alternative to the traditional oxidative displacement.

  DOI：

  10.1055/s-0033-1339293
• 作为产物：
  描述：

  在 benzyl triethylammonium azide 、 四丁基溴化铵 、 碘 作用下， 以 四氢呋喃 、 2-甲基四氢呋喃 为溶剂， 反应 20.0h， 生成 [(2R,3S,4S,5R)-2-azido-5-(2,4-dioxopyrimidin-1-yl)-4-methyl-3-(2-methylpropanoyloxy)oxolan-2-yl]methyl 2-methylpropanoate
  参考文献：
  名称：

  Synthesis of (4′R)-Azido-(2′R)-2′-Deoxy-2′-C-Methyluridine and Its Esters by Direct Iodide Displacement

  摘要：

  The synthesis of an anti-infective nucleoside intermediate was accomplished through direct iodine displacement at C-5' by a tetrabutylammonium carboxylate. This approach constitutes a more efficient alternative to the traditional oxidative displacement.

  DOI：

  10.1055/s-0033-1339293

文献信息

• New Synthesis of 2′,4′-Functionalized Nucleotides via Stereospecific Hydrogenation and Azidation Reactions
  作者：Ioannis Houpis、Sebastien Lemaire、Vittorio Farina、Tingting Xiao、Renmao Liu、Ulrike Nettekoven、Youchu Wang

  DOI：10.1055/s-0032-1317715

  日期：——

  The synthesis of an anti-infective nucleoside derivative was accomplished through selective hydrogenation using an achiral ligand to establish the stereochemistry of the 2′ stereogenic center. The quaternary 4′ center was introduced through stereoselective epoxidation with dimethyl dioxirane followed by a regioselective, stereospecific epoxide opening with trimethylsilyl azide.

  抗感染核苷衍生物的合成是通过使用非手性配体的选择性氢化来完成的，以建立 2' 立体中心的立体化学。通过使用二甲基二环氧乙烷进行立体选择性环氧化，然后使用三甲基甲硅烷基叠氮化物进行区域选择性立体选择性环氧化物开环，引入四元 4' 中心。
• Discovery of 4′-azido-2′-deoxy-2′-C-methyl cytidine and prodrugs thereof: A potent inhibitor of Hepatitis C virus replication
  作者：Magnus Nilsson、Genadiy Kalayanov、Anna Winqvist、Pedro Pinho、Christian Sund、Xiao-Xiong Zhou、Horst Wähling、Anna-Karin Belfrage、Michael Pelcman、Tatiana Agback、Kurt Benckestock、Kristina Wikström、Mirva Boothee、Anneli Lindqvist、Christina Rydegård、Tim H.M. Jonckers、Koen Vandyck、Pierre Raboisson、Tse-I Lin、Sophie Lachau-Durand、Herman de Kock、David B. Smith、Joseph A. Martin、Klaus Klumpp、Kenneth Simmen、Lotta Vrang、Ylva Terelius、Bertil Samuelsson、Åsa Rosenquist、Nils Gunnar Johansson

  DOI：10.1016/j.bmcl.2012.03.021

  日期：2012.5

  4'-Azido-2'-deoxy-2'-methylcytidine (14) is a potent nucleoside inhibitor of the HCV NS5B RNA-dependent RNA polymerase, displaying an EC50 value of 1.2 mu M and showing moderate in vivo bioavailability in rat (F = 14%). Here we describe the synthesis and biological evaluation of 4'-azido-2'-deoxy-2'-methylcytidine and prodrug derivatives thereof. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis of (4′R)-Azido-(2′R)-2′-Deoxy-2′-C-Methyluridine and Its Esters by Direct Iodide Displacement
  作者：Cyril Benhaim、Sébastien Lemaire、Tim Gaekens、Tom Govaerts、Ioannis Houpis、Peter Reniers、Anja Van Looy、Wim Vermeulen、Sebastian Bernhardt、Coura Diène、Paul Knochel、Vittorio Farina

  DOI：10.1055/s-0033-1339293

  日期：——

  The synthesis of an anti-infective nucleoside intermediate was accomplished through direct iodine displacement at C-5' by a tetrabutylammonium carboxylate. This approach constitutes a more efficient alternative to the traditional oxidative displacement.