N²,3-etheno-O⁶-benzylguanosine | 108060-84-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N²,3-etheno-O⁶-benzylguanosine
• 英文别名: O⁶-Benzyl-N²,3-ethenoguanosine；(2R,3R,4S,5R)-2-(4-(benzyloxy)-1H-imidazo[2,1-b]purin-1-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol；(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(4-phenylmethoxyimidazo[2,1-b]purin-1-yl)oxolane-3,4-diol
• CAS: 108060-84-0
• 化学式: C₁₉H₁₉N₅O₅
• 分子量: 397.39
• InChiKey: NVQPPRXKVSLORP-SCFUHWHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  127
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N²,3-etheno-O⁶-benzylguanosine 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 水 为溶剂， 反应 48.0h， 以85%的产率得到N²,3-Ethenoguanosine
  参考文献：
  名称：

  N2,3-etheno-2'-deoxyguanosine [8,9-dihydro-9-oxo-2'-deoxy-3-.beta.-D-ribofuranosylimidazo[2,1-b]purine]: a practical synthesis and characterization

  摘要：

  The literature methods for the syntheses of N2,3-etheno-2'-deoxyguanosine (1a) and its 5'-O-phosphate are associated with very low overall yields. We now describe a route starting in the riboside series that permits the production of 1a in practical quantities and has allowed its complete chemical characterization for the first time. O6-Benzylguanosine (6b) when treated with bromoacetaldehyde under conditions of continuous buffering gives the N2,3-etheno derivative 7b in 48% yield. The 3',5'-O-(1,1,3,3-tetraisopropyldisiloxa-1,3-diyl) derivative (8b, 89 % yield) of 7b when allowed to react with phenyl chlorothionoformate led to the corresponding 2' ester (10,50%). 2'-Deoxygenation of 10 by the Barton procedure then afforded 65% of 11, and deprotection of the latter (Bu4N+F-) gave 12 quantitatively. Catalytic hydrogenation of 12 then produced pure la in 86% yield. Stability studies on la have confirmed its exquisite sensitivity to acid and demonstrated its relative stability to alkali and the other reagents used in automated DNA synthesis (phosphoramidate method).

  DOI：

  10.1021/jo00061a033
• 作为产物：
  描述：

  鸟苷 在 sodium acetate buffer 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 28.0h， 生成 N²,3-etheno-O⁶-benzylguanosine
  参考文献：
  名称：

  Synthesis and properties of N2,3-ethenoguanosine and N2,3-ethenoguanosine 5'-diphosphate

  摘要：

  DOI：

  10.1021/jo00388a007

文献信息

• [EN] CYCLIC DI-NUCLEOTIDE COMPOUNDS AS STING AGONISTS<br/>[FR] COMPOSÉS DINUCLÉOTIDIQUES CYCLIQUES UTILISÉS COMME AGONISTES STING
  申请人：MERCK SHARP & DOHME

  公开号：WO2019125974A1

  公开（公告）日：2019-06-27

  A class of polycyclic compounds of general formula (I), wherein Base1, Base2, Y, Za, Xa, Xa1, Xb, Xb1, Xc, Xc1, Xd, Xd1, R1, R1a, R2, R2a, R3, R4, R4a, R5, R6, R6a, R7, R7a, R8, R8a, and R9 are defined herein, that may be useful as inductors of type I interferon production, specifically as STING active agents, are provided. Also provided are processes for the synthesis and use of compounds.

  一类具有通用公式（I）的多环化合物的类别，其中Base1，Base2，Y，Za，Xa，Xa1，Xb，Xb1，Xc，Xc1，Xd，Xd1，R1，R1a，R2，R2a，R3，R4，R4a，R5，R6，R6a，R7，R7a，R8，R8a和R9按本说明书中定义，可能对作为I型干扰素产生的诱导剂特别有用，具体作为STING激活剂。还提供了合成和使用化合物的过程。
• CYCLIC DI-NUCLEOTIDE COMPOUNDS AS STING AGONISTS
  申请人：MERCK SHARP & DOHME CORP.

  公开号：EP3727401A1

  公开（公告）日：2020-10-28
• N2,3-etheno-2'-deoxyguanosine [8,9-dihydro-9-oxo-2'-deoxy-3-.beta.-D-ribofuranosylimidazo[2,1-b]purine]: a practical synthesis and characterization
  作者：Rajesh Khazanchi、Pei Lin Yu、Francis Johnson

  DOI：10.1021/jo00061a033

  日期：1993.4

  The literature methods for the syntheses of N2,3-etheno-2'-deoxyguanosine (1a) and its 5'-O-phosphate are associated with very low overall yields. We now describe a route starting in the riboside series that permits the production of 1a in practical quantities and has allowed its complete chemical characterization for the first time. O6-Benzylguanosine (6b) when treated with bromoacetaldehyde under conditions of continuous buffering gives the N2,3-etheno derivative 7b in 48% yield. The 3',5'-O-(1,1,3,3-tetraisopropyldisiloxa-1,3-diyl) derivative (8b, 89 % yield) of 7b when allowed to react with phenyl chlorothionoformate led to the corresponding 2' ester (10,50%). 2'-Deoxygenation of 10 by the Barton procedure then afforded 65% of 11, and deprotection of the latter (Bu4N+F-) gave 12 quantitatively. Catalytic hydrogenation of 12 then produced pure la in 86% yield. Stability studies on la have confirmed its exquisite sensitivity to acid and demonstrated its relative stability to alkali and the other reagents used in automated DNA synthesis (phosphoramidate method).
• Synthesis and properties of N2,3-ethenoguanosine and N2,3-ethenoguanosine 5'-diphosphate
  作者：Jaroslaw T. Kusmierek、David E. Jensen、Sylvia J. Spengler、Ryszard Stolarski、B. Singer

  DOI：10.1021/jo00388a007

  日期：1987.6