3′-deoxy-3′,4′-didehydrouridine-5′-aldehyde | 26301-97-3

• 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: 3′-deoxy-3′,4′-didehydrouridine-5′-aldehyde
• 英文别名: 3'-deoxy-3',4'-didehydrouridine-5'-aldehyde；(2R,3R)-2-(2,4-dioxopyrimidin-1-yl)-3-hydroxy-2,3-dihydrofuran-5-carbaldehyde
• CAS: 26301-97-3
• 化学式: C₉H₈N₂O₅
• 分子量: 224.173
• InChiKey: PXUFGDOYQZQYIG-HTRCEHHLSA-N

物化性质

• 密度：
  1.750±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  95.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3′-deoxy-3′,4′-didehydrouridine-5′-aldehyde 在 sodium tetrahydroborate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 1'-uracil-3'-deoxy-3',4'-didehydroribonucleoside
  参考文献：
  名称：

  由DMF二甲基乙缩醛介导的3'-脱氧-3'，4'-二氢核苷的费勒型烯丙基重排：直接进入4'-烷氧基-2'，3'-二氢氢化物2，，3'-二脱氧核苷

  摘要：

  描述了通过DMF二甲基乙缩醛介导的3'-脱氧-3'，4'-二氢核苷的烯丙基重排，直接合成差向异构4'-烷氧基取代的2'，3'-二氢-2'，3'-二氧核苷。

  DOI：

  10.1021/ol201519a
• 作为产物：
  描述：

  尿嘧啶核苷 在 吡啶 、 对甲苯磺酸 、 二甲基亚砜 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.25h， 生成 3′-deoxy-3′,4′-didehydrouridine-5′-aldehyde
  参考文献：
  名称：

  [EN] PROTECTED DEOXYDIDEHYDRO-NUCLEOSIDES
  [FR] DÉSOXYDIDÉHYDRO-NUCLÉOSIDES PROTÉGÉS

  摘要：

  本发明提供了式(I)或式(Ia)的化合物，这些化合物在合成潜在的抗病毒药物，如3'-去氧-3',4'-二脱氢胞嘧啶三磷酸（ddhCTP）中是有用的中间体。

  公开号：

  WO2022123501A1

文献信息

• Biogenesis of the Unique 4′,5′-Dehydronucleoside of the Uridyl Peptide Antibiotic Pacidamycin
  作者：Amany E. Ragab、Sabine Grüschow、Daniel R. Tromans、Rebecca J. M. Goss

  DOI：10.1021/ja206163j

  日期：2011.10.5

  The pacidamycins belong to a class of antimicrobial nucleoside antibiotics that act by inhibiting the clinically unexploited target translocase I, a key enzyme in peptidoglycan assembly. As with other nucleoside antibiotics, the pacidamycin 4',5'-dehydronucleoside portion is an essential pharmacophore. Here we show that the biosynthesis of the pacidamycin nucleoside in Streptomyces coeruleorubidus proceeds through three steps from uridine. The transformations involve oxidation of the 5'-alcohol by Pac11, transamination of the resulting aldehyde by Pac5, and dehydration by the Cupin-domain protein Pac13.
• Straightforward synthesis of 3′-deoxy-3′,4′-didehydronucleoside-5′-aldehydes via 2′,3′-O-orthoester group elimination: a simple route to 3′,4′-didehydronucleosides
  作者：Magdalena Petrová、Miloš Buděšínský、Ivan Rosenberg

  DOI：10.1016/j.tetlet.2010.10.117

  日期：2010.12

  Straightforward, high-yielding syntheses of 3'-deoxy-3',4'-didehydronucleoside-5'-aldehydes and 3'-deoxy-3',4'-didehydronucleosides starting from 2',3'-O-orthoester derivatives of ribonucleosides are described. (C) 2010 Elsevier Ltd. All rights reserved.
• 5′-Epimeric 3′-deoxy-3′,4′-didehydronucleoside-5′-C-phosphonates: synthesis and structural assignment by NMR and X-ray analyses
  作者：Magdalena Petrová、Miloš Buděšínský、Blanka Klepetářová、Ivan Rosenberg

  DOI：10.1016/j.tet.2011.04.037

  日期：2011.6

  Epimeric 5'-(RS) dialkyl 3'-deoxy-3',4'-didehydro-5'-C-phosphonates were prepared by nucleophilic addition of various dialkyl phosphites to 3'-deoxy-3',4'-didehydronucleoside-5'-aldehydes. Whereas direct NMR configuration assignment for the C5' atom bearing the phosphoryl and hydroxy groups using the J (P,H4') and J (H5',H4') coupling constants is impossible due to the absence of the H4' atom, successful separation, crystallisation and X-ray crystallographic analysis of a pair of epimeric 5'-C-phosphonates, followed by correlation with a series of NMR parameters, led to efficacious configuration assignment of individual epimers in the mixtures. (C) 2011 Published by Elsevier Ltd.
• [EN] ANTI-VIRAL AND ANTI-TUMORAL COMPOUNDS<br/>[FR] COMPOSÉS ANTI-VIRAUX ET ANTI-TUMORAUX
  申请人：YEDA RES & DEV

  公开号：WO2022038539A3

  公开（公告）日：2022-03-31
• A Ferrier-Type Allylic Rearrangement of 3′-Deoxy-3′,4′-didehydronucleosides Mediated by DMF Dimethyl Acetal: Direct Access to 4′-Alkoxy-2′,3′-didehydro-2′,3′-dideoxynucleosides
  作者：Magdalena Petrová、Miloš Buděšínský、Eva Zborníková、Pavel Fiedler、Ivan Rosenberg

  DOI：10.1021/ol201519a

  日期：2011.8.19

  A straightforward synthesis of epimeric 4′-alkoxy-substituted 2′,3′-didehydro-2′,3′-dideoxynucleosides via a DMF dimethyl acetal mediated allylic rearrangement of 3′-deoxy-3′,4′-didehydronucleosides is described.

  描述了通过DMF二甲基乙缩醛介导的3'-脱氧-3'，4'-二氢核苷的烯丙基重排，直接合成差向异构4'-烷氧基取代的2'，3'-二氢-2'，3'-二氧核苷。