6,7-diphenyl-2,4-bis-trimethylsilanyloxy-pteridine | 50255-88-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 英文名称: 6,7-diphenyl-2,4-bis-trimethylsilanyloxy-pteridine
• 英文别名: 6,7-Diphenyl-2,4-bis[(trimethylsilyl)oxy]pteridine；(6,7-diphenyl-2-trimethylsilyloxypteridin-4-yl)oxy-trimethylsilane
• CAS: 50255-88-4
• 化学式: C₂₄H₂₈N₄O₂Si₂
• 分子量: 460.683
• InChiKey: IJTMSLSSANCUOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.18
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  70
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6,7-diphenyl-2,4-bis-trimethylsilanyloxy-pteridine 在 吡啶 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三氟化硼乙醚 、 三正丁基氢锡 、 sodium methylate 、 一水合肼 、 溶剂黄146 作用下， 以 吡啶 、 乙酸乙酯 、 甲苯 、 乙腈 为溶剂， 反应 25.67h， 生成 1-(2-deoxy-5-O-p-monomethoxytrityl-β-D-threo-pentofuranosyl)-6,7-diphenyllumazine
  参考文献：
  名称：

  Nucleosides. LIV¹Synthesis and Properties of 3′-Azido- and 2′,3′-Dideoxy-6,7-diphenyllumazine Nucleosides

  摘要：

  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.

  DOI：

  10.1080/15257779408013278
• 作为产物：
  描述：

  2,4(1H,3H)-蝶啶二酮,6,7-二苯基- 、 六甲基二硅氮烷 生成 6,7-diphenyl-2,4-bis-trimethylsilanyloxy-pteridine
  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

• Synthesis and properties of 2,2′-anhydro-N-3-lumazine nucleosides
  作者：Hermann Lutz、Wolfgang Pfleiderer

  DOI：10.1016/0008-6215(84)85279-9

  日期：1984.7

  conditions led to selective 2,2′-cyclization but no products possessing the less favored 4,2′-structure were obtained. The best yields of 2,2′-anhydro-3-β- d -arabinofuranosyllumazines were obtained from 3-(2,3- O -carbonyl-5- O -trityl-β- d -ribofuranosyl)lumazines in an imidazole-catalyzed reaction at elevated temperatures. Base hydrolysis of the 2,2′-bond allowed the synthesis of 3-β- d -arabinofuranosyllumazines

  摘要研究了3-β-d-核呋喃呋喃糖基鲁嗪及其6,7-二甲基和二苯基衍生物与糖苷配基的相邻羰基形成脱水核苷的反应。各种条件导致选择性的2,2'-环化，但未获得具有较不受欢迎的4,2'-结构的产物。在咪唑催化下，由3-（2,3- O-羰基-5-O-三苯甲基-β-d-呋喃呋喃糖基）lumazines获得2,2'-脱水-3-β-d-阿拉伯呋喃糖基lumazines的最佳收率在高温下反应。2，2′-键的碱水解允许合成3-β-d-阿拉伯呋喃糖基lumazines。
• 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.
• Pteridine Nucleosides—New Versatile Building Blocks in Oligonucleotide Synthesis
  作者：Ramamurthy Charubala、Juris Maurinsh、Angelika Rösler、Manuel Melguizo、Oliver Jungmann、Margarete Gottlieb、Jörg Lehbauer、Mary Hawkins、Wolfgang Pfleiderer

  DOI：10.1080/07328319708006188

  日期：1997.7

  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.