[(2R,3R,4R,5R)-5-(5-amino-7-oxo-6H-triazolo[4,5-d]pyrimidin-3-yl)-3,4-dibenzoyloxy-tetrahydrofuran-2-yl]methyl benzoate | 38874-35-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4R,5R)-5-(5-amino-7-oxo-6H-triazolo[4,5-d]pyrimidin-3-yl)-3,4-dibenzoyloxy-tetrahydrofuran-2-yl]methyl benzoate
• 英文别名: [(2R,3R,4R,5R)-5-(5-amino-7-oxo-6H-triazolo[4,5-d]pyrimidin-3-yl)-3,4-dibenzoyloxyoxolan-2-yl]methyl benzoate
• CAS: 38874-35-0
• 化学式: C₃₀H₂₄N₆O₈
• 分子量: 596.556
• InChiKey: KKNBTIMRZNRCKW-HUBRGWSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  186
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4R,5R)-5-(5-amino-7-oxo-6H-triazolo[4,5-d]pyrimidin-3-yl)-3,4-dibenzoyloxy-tetrahydrofuran-2-yl]methyl benzoate 在 氨 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 5-氨基-3-[3,4-二羟基-5-(羟基甲基)四氢呋喃-2-基]-2H-三唑并[4,5-e]嘧啶-7-酮
  参考文献：
  名称：

  High-Throughput Five Minute Microwave Accelerated Glycosylation Approach to the Synthesis of Nucleoside Libraries

  摘要：

  [GRAPHICS]The Vorbruggen glycosylation reaction was adapted into a one-step 5 min/130 degrees C microwave assisted reaction. Triethanolamine in acetontrile containing 2% water was determined to be optimal for the neutralization of trimethylsilyl triflate allowing for direct MPLC purification of the reaction mixture. When coupled with a NH3/methanol deprotection reaction, a high-throughput method of nucleoside library synthesis was enabled. The method was demonstrated by examining the ribosylation of 48 nitrogen containing heteroaromatic bases that included 25 purines, four pyrazolopyrimidines, two 8-azapurines, one 2-azapurine, two imidazopyridines, two benzimidazoles, three imidazoles, three 1,2,4-triazoles, two pyrimidines, two 3-deazapyrimidines, one quinazolinedione, and one alloxazine. Of these, 32 yielded single regioisomer products, and six resulted in separable mixtures. Seven examples provided inseparable regioisomer mixtures of -two to three compounds (16 nucleosides), and three examples failed to yield isolable products. For the 45 single isomers isolated, the average two-step overall yield +/- SD was 26 +/- 16%, and the average purity +/- SD was 95 +/- 6%. A total of 58 different nucleosides were prepared of which 15 had not previously been accessed directly from glycosylation/deprotection of a readily available base.

  DOI：

  10.1021/jo061885l
• 作为产物：
  描述：

  1-乙酰氧基-2,3,5-三苯甲酰氧基-1-beta-D-呋喃核糖 、 8-氮鸟嘌呤 在 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以57%的产率得到[(2R,3R,4R,5R)-5-(5-amino-7-oxo-6H-triazolo[4,5-d]pyrimidin-3-yl)-3,4-dibenzoyloxy-tetrahydrofuran-2-yl]methyl benzoate
  参考文献：
  名称：

  [EN] STING MODULATOR COMPOUNDS, AND METHODS OF MAKING AND USING
  [FR] COMPOSÉS MODULATEURS DE STING, ET PROCÉDÉS DE FABRICATION ET D'UTILISATION

  摘要：

  本公开提供STING调节剂/激动剂，以及合成方法和用于预防或治疗癌症和其他STING相关疾病的方法。本公开涉及由式(I)表示的化合物：其中每个符号如描述中定义，或其药用可接受盐。

  公开号：

  WO2019092660A1

文献信息

• Identification of Novel Carbocyclic Pyrimidine Cyclic Dinucleotide STING Agonists for Antitumor Immunotherapy Using Systemic Intravenous Route
  作者：Stepan Vyskocil、David Cardin、Jeffrey Ciavarri、Joe Conlon、Courtney Cullis、Dylan England、Rachel Gershman、Kenneth Gigstad、Krista Gipson、Alexandra Gould、Paul Greenspan、Robert Griffin、Nanda Gulavita、Sean Harrison、Zhigen Hu、Yongbo Hu、Akito Hata、Jian Huang、Shih-Chung Huang、Dave Janowick、Matthew Jones、Vihren Kolev、Steven P. Langston、Hong Myung Lee、Gang Li、David Lok、Liting Ma、Doanh Mai、Jenna Malley、Atsushi Matsuda、Hirotake Mizutani、Miho Mizutani、Nina Molchanova、Elise Nunes、Sandeep Pusalkar、Christelle Renou、Scott Rowland、Yosuke Sato、Michael Shaw、Luhua Shen、Zhan Shi、Robert Skene、Francois Soucy、Steve Stroud、He Xu、Tianlin Xu、Adnan O. Abu-Yousif、Ji Zhang

  DOI：10.1021/acs.jmedchem.1c00374

  日期：2021.5.27
• STING MODULATOR COMPOUNDS, AND METHODS OF MAKING AND USING
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP3707151A1

  公开（公告）日：2020-09-16