methyl 1-(2',3',3''-tri-O-benzoyl-apio-β-D-furanosyl)triazole-5-carboxylate | 39925-13-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 三唑核糖核苷和核糖核苷酸
• 英文名称: methyl 1-(2',3',3''-tri-O-benzoyl-apio-β-D-furanosyl)triazole-5-carboxylate
• 英文别名: 2-(tri-O-benzoyl-β-D-ribofuranosyl)-2H-[1,2,4]triazole-3-carboxylic acid methyl ester；1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,2,4-triazole-5-carboxylic acid methyl ester；methyl 2-[(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(benzoyloxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxylate
• CAS: 39925-13-8
• 化学式: C₃₀H₂₅N₃O₉
• 分子量: 571.543
• InChiKey: IZMPKIHVDPRUTQ-PMHJDTQVSA-N

物化性质

• 沸点：
  729.0±70.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  145
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl 1-(2',3',3''-tri-O-benzoyl-apio-β-D-furanosyl)triazole-5-carboxylate 在 氨 作用下， 以 甲醇 为溶剂， 生成 利巴韦林杂质G
  参考文献：
  名称：

  Vorbrueggen, Helmut; Krolikiewicz, Konrad; Bennua, Baerbel, Chemische Berichte, 1981, vol. 114, # 4, p. 1234 - 1255

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 3'-O-benzoyl-2,3-O-isopropylidene-β-D-apiofuranoside 在 吡啶 、 4-二甲氨基吡啶 、 ammonium sulfate 、 Dowex 50H⁺ 、 硫酸 、 溶剂黄146 、 六甲基二硅氮烷 作用下， 以 甲醇 为溶剂， 反应 82.5h， 生成 methyl 1-(2',3',3''-tri-O-benzoyl-apio-β-D-furanosyl)triazole-5-carboxylate
  参考文献：
  名称：

  噻唑-4-羧酰胺和1,2,4-三唑-3-羧酰胺的新型Apio核苷的合成及生物学评估

  摘要：

  鉴于吡咯核苷和apio-dideoxy核苷的生物活性，使用2,3-O-异亚丙基-apio-β-d-呋喃糖合成了具有噻唑和三唑碱基部分的新型apio核苷类似物（1和2），它是由d-甘露糖制成的。

  DOI：

  10.1081/ncn-120037666

文献信息

• High-Throughput Five Minute Microwave Accelerated Glycosylation Approach to the Synthesis of Nucleoside Libraries
  作者：Brett C. Bookser、Nicholas B. Raffaele

  DOI：10.1021/jo061885l

  日期：2007.1.1

  [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.
• USRE29835E
  申请人：——

  公开号：USRE29835E

  公开（公告）日：1978-11-14
• Synthesis and Biological Evaluation of Novel Apio Nucleosides with Thiazole‐4‐carboxamide and 1,2,4‐Triazole‐3‐carboxamide
  作者：Myong Jung Kim、Lak Shin Jeong、Joong Hyup Kim、Ji Hye Shin、Soon Yong Chung、Sang Kook Lee、Moon Woo Chun

  DOI：10.1081/ncn-120037666

  日期：2004.12.31

  In view of biological activities of azole nucleosides and apio‐dideoxynucleoside, novel apio nucleoside analogues (1 and 2) with thiazole and triazole base moiety were synthesized using 2,3‐O‐isopropylidene‐apio‐β‐d‐furanose (3), which was prepared from d‐mannose.

  鉴于吡咯核苷和apio-dideoxy核苷的生物活性，使用2,3-O-异亚丙基-apio-β-d-呋喃糖合成了具有噻唑和三唑碱基部分的新型apio核苷类似物（1和2），它是由d-甘露糖制成的。
• Vorbrueggen, Helmut; Krolikiewicz, Konrad; Bennua, Baerbel, Chemische Berichte, 1981, vol. 114, # 4, p. 1234 - 1255
  作者：Vorbrueggen, Helmut、Krolikiewicz, Konrad、Bennua, Baerbel

  DOI：——

  日期：——