tri-O-benzoyl-1-(6-methylsulfanyl-purin-9-yl)-β-D-1-deoxy-ribofuranose | 66782-10-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: tri-O-benzoyl-1-(6-methylsulfanyl-purin-9-yl)-β-D-1-deoxy-ribofuranose
• 英文别名: 2',3',5'-Tri-O-bezoyl-6-thioinosin；[(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(6-methylsulfanylpurin-9-yl)oxolan-2-yl]methyl benzoate
• CAS: 66782-10-3
• 化学式: C₃₂H₂₆N₄O₇S
• 分子量: 610.647
• InChiKey: WELFEAKBSXHOSG-CTDWIVFPSA-N

物化性质

• 沸点：
  783.0±70.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  44.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  131.73
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  tri-O-benzoyl-1-(6-methylsulfanyl-purin-9-yl)-β-D-1-deoxy-ribofuranose 在 sodium hydroxide 、 potassium permanganate 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 8.5h， 生成 (2R,3s,4r,5r)-2-(羟基甲基)-5-(6-甲基-9h-嘌呤-9-基)四氢呋喃-3,4-二醇
  参考文献：
  名称：

  Yamane, Akira; Matsuda, Akira; Ueda, Tohru, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 1, p. 150 - 156

  摘要：

  DOI：
• 作为产物：
  描述：

  2',3',5'-tri-O-benzoyl-6-thioinosine 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 tri-O-benzoyl-1-(6-methylsulfanyl-purin-9-yl)-β-D-1-deoxy-ribofuranose
  参考文献：
  名称：

  Yamane, Akira; Matsuda, Akira; Ueda, Tohru, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 1, p. 150 - 156

  摘要：

  DOI：

文献信息

• A new direct glycosylation of pyrimidine, pyrazole, imidazole and purine heterocycles via their N-tetrahydropyranyl (THP) derivatives
  作者：Stefano Manfredini、Pier Giovanni Baraldi、Rita Bazzanini、Mario Guarneri、Daniele Simoni

  DOI：10.1039/c39940000583

  日期：——

  Pyrimidine, pyrazole, imidazole and purine N-tetrahydropyranyl (THP) derivatives have been converted in one-pot and in a regio- and stereo-selective manner into the corresponding β-D-2′,3′,5′-tri-O-benzoyl ribofuranosyl nucleoside derivatives on treatment with 1-β-acetyl-2′,3′,5′-tri-O-benzoyl-ribofuranose, hexamethyldisilazane (HMDS), trimethylsilyl chloride (TMSCI), and trimethylsilyl triflate (TMST).

  嘧啶、哌唑、咪唑和嘌呤N-四氢吡喃基（THP）衍生物在一锅反应中以区域和立体选择性方式转化为相应的β-D-2′,3′,5′-三-O-苯甲酰核糖苷衍生物，反应中使用了1-β-乙酰-2′,3′,5′-三-O-苯甲酰核糖、六甲基二硅氮烷（HMDS）、三甲基氯硅烷（TMSCI）和三甲基硅烷三氟甲磺酸盐（TMST）。
• 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.
• UEHDA, TORU;MATSUDA, AKIRA;YAMANEH, AKIRA
  作者：UEHDA, TORU、MATSUDA, AKIRA、YAMANEH, AKIRA

  DOI：——

  日期：——