3'-deoxy-3',4'-didehydro-2-N-isobutyrylguanosine-5'-aldehyde | 1262202-25-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 3'-deoxy-3',4'-didehydro-2-N-isobutyrylguanosine-5'-aldehyde
• 英文别名: N-[9-[(2R,3R)-5-formyl-3-hydroxy-2,3-dihydrofuran-2-yl]-6-oxo-1H-purin-2-yl]-2-methylpropanamide
• CAS: 1262202-25-4
• 化学式: C₁₄H₁₅N₅O₅
• 分子量: 333.304
• InChiKey: YLYPENSLJQLJAT-AMIZOPFISA-N

物化性质

• 密度：
  1.70±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  135
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3'-deoxy-3',4'-didehydro-2-N-isobutyrylguanosine-5'-aldehyde 在 甲醇 、 sodium tetrahydroborate 、 甲胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 3'-deoxy-3',4'-didehydroriboside
  参考文献：
  名称：

  Straightforward synthesis of 3′-deoxy-3′,4′-didehydronucleoside-5′-aldehydes via 2′,3′-O-orthoester group elimination: a simple route to 3′,4′-didehydronucleosides

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2010.10.117
• 作为产物：
  描述：

  2',3'-di-O-methoxymethylidene-2-N-isobutyrylguanosine 在 吡啶 、 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 N,N-二甲基甲酰胺 为溶剂， 生成 3'-deoxy-3',4'-didehydro-2-N-isobutyrylguanosine-5'-aldehyde
  参考文献：
  名称：

  Straightforward synthesis of 3′-deoxy-3′,4′-didehydronucleoside-5′-aldehydes via 2′,3′-O-orthoester group elimination: a simple route to 3′,4′-didehydronucleosides

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2010.10.117

文献信息

• 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
• 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.