1-[O³,O⁵-bis-(4-methyl-benzoyl)-α-L-erythro-2-deoxy-pentofuranosyl]-1H-pteridine-2,4-dione | 35777-63-0

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 1-[O³,O⁵-bis-(4-methyl-benzoyl)-α-L-erythro-2-deoxy-pentofuranosyl]-1H-pteridine-2,4-dione
• CAS: 35777-63-0
• 化学式: C₂₇H₂₄N₄O₇
• 分子量: 516.51
• InChiKey: GLWABJDNHASBNN-HBMCJLEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.47
• 重原子数：
  38.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  142.47
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  2,4-二羟基蝶啶 生成 1-[O³,O⁵-bis-(4-methyl-benzoyl)-α-L-erythro-2-deoxy-pentofuranosyl]-1H-pteridine-2,4-dione
  参考文献：
  名称：

  Pteridine Nucleosides—New Versatile Building Blocks in Oligonucleotide Synthesis

  摘要：

  Chemical syntheses of 1-(2-deoxy-beta-D-ribofuranosyl)lumazines and isopterins as well as 8-(2-deoxy-beta-D-ribofuranosyl)-4-amino-7(8H)pteridones and -isoxanthopterins have been developed to make the structural analogs of the naturally occurring 2'-deoxyribonucleosides in the pteridine series available. The corresponding phosphoramidites have been used in machine-aided solid-support syntheses leading to new types of fluorescence labeled oligonucleotides. The effects of the various fluorophors on duplex formation and as labels for enzyme reactions is demonstrated.

  DOI：

  10.1080/07328319708006188

文献信息

• Nucleotides. Part LIV. Synthesis of condensedN1-(2?-deoxy-?-D-ribofuranosyl)lumazines, New fluorescent building blocks in oligonucleotide synthesis
  作者：Angelika Rosler、Wolfgang Pfleiderer

  DOI：10.1002/hlca.19970800611

  日期：1997.9.22

  3′-(2-cyanoethyI diisopropylphosphoramidites) 34–39 which function as monomeric building block in oligonucleotide syntheses as well as into the 3′-(hydrogen succinates) 40–45 which can be used for coupling with the solid-support material. A series of lumazine-modified oligonucleotides were synthesized and the influence of the new nucleobases on the stability of duplex formation studied by measuring the Tm values

  各种缩合areno [克] lumazine衍生物2，3，和5 - 7合成作为糖基化反应的新的荧光苷元与2-脱氧-3，5-二- Ö - （p甲苯甲酰）-α/β-D-在Hilbert - Johnson - Birkofer反应中，赤型-五氟呋喃糖酰氯（10）形成相应的N 1-（2'-deoxyribonucleosides）15 – 21。的βd端基异构体15，17，19，和21被解封为24 – 27，并与N 1-（2'-脱氧-β-D-呋喃呋喃糖基）lumazine（22）及其6，6，7-二苯基衍生物23一起在5'-位被二甲氧基三苯甲基化为28-33。然后将这些中间体转化成3' - （2- cyanoethyI diisopropylphosphoramidites）34 - 39，其功能如在寡核苷酸合成以及进3单体结构单元' - （氢琥珀酸酯）40 - 45可用于与固相支持材料偶联。合成
• Nucleosides. LIV¹Synthesis and Properties of 3′-Azido- and 2′,3′-Dideoxy-6,7-diphenyllumazine Nucleosides
  作者：Xiaodong Cao、Wolfgang Pfleiderer

  DOI：10.1080/15257779408013278

  日期：1994.3

  The best approach for the synthesis of 1-(3-azido-2,3-dideoxy-beta-D-erythro-pentofuranosyl)lumazine (5) and its 6,7-dimethyl- (4) and 6,7-diphenyl derivatives (3) has been found in the interconversion of the corresponding 1-(2-deoxy-beta-D-threo-pentofuranosyl)-lumazines. Monomethoxytritylation at the 5'-position (1 7, 3 4, 4 9) followed by mesylation at the 3'-OH group and subsequent nucleophilic displacement by lithium azide afforded 1 9, 2 9 and 4 7 which were deprotected by acid treatment to give 3-5 in good yields. The syntheses of 1-(2,3-dideoxy-beta-D- glycero-pentofuranosyl)-6,7-diphenyllumazine (6) and its 6,7-dimethyl derivative (7) were achieved from 1-(2-deoxy-beta-D-erythro-pentofuranosyl)- 6,7-diphenyllumazine and the corresponding 6,7-dimethyllumazine (2 6) via their 5'-O-p-toluoyl- (2 0, 3 0), and 3'-deoxy-3'-iodo derivatives (2 4, 3 1) to form, after radical dehalogenation and final deprotection, 6 and 7. The newly synthesized lumazine nucleosides have been characterized by elemental analyses, UV- and NMR spectra.