(2R,3S,4R,5R)-2-(羟基甲基)-5-嘌呤-7-基四氢呋喃-3,4-二醇 | 2149-71-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (2R,3S,4R,5R)-2-(羟基甲基)-5-嘌呤-7-基四氢呋喃-3,4-二醇
• 英文名称: 1-purin-7-yl-β-D-1-deoxy-ribofuranose
• 英文别名: 7-β-D-ribofuranosyl-7H-purine；7-(β-D-Ribofuranosyl)purin；7-beta-D-Ribofuranosyl-7H-purine；(2R,3S,4R,5R)-2-(hydroxymethyl)-5-purin-7-yloxolane-3,4-diol
• CAS: 2149-71-5
• 化学式: C₁₀H₁₂N₄O₄
• 分子量: 252.23
• InChiKey: TXDJXYCWUSYGSN-FDDDBJFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  7

安全信息

• 海关编码：
  2934999090

反应信息

• 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 、 嘌呤 在 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 、 氨 作用下， 以 乙腈 、 甲醇 为溶剂， 反应 16.08h， 生成 9 - (Β-D -呋喃核糖)嘌呤 、 (2R,3S,4R,5R)-2-(羟基甲基)-5-嘌呤-7-基四氢呋喃-3,4-二醇
  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

文献信息

• Certain adenosine 5'-carboxamide derivatives
  申请人：CIBA-GEIGY AG

  公开号：EP0277917A2

  公开（公告）日：1988-08-10

  The compounds of the formula I wherein R represents hydrogen or lower alkyl; R¹ represents cyclo­alkyl, cycloalkyl-lower alkyl, 2-norbornanyl, 2-norbornanyl-lower alkyl, aryl, aryl-lower alkyl, aryl-cycloalkyl, 9-fluorenyl, diaryl-lower alkyl or 9-fluorenyl-lower alkyl; or R¹ represents a bicyclic benzo-fused 5- or 6-membered saturated carbocyclic radical or a benzo-fused 5- or 6-membered saturated heterocyclic radical containing a heteroatom selected from oxygen and sulfur which is directly attached to the fused benzene ring, any said bicyclic radical being unsubstituted or substituted on the benzo portion by lower alkyl, lower alkoxy, hydroxy, halogen or trifluoromethyl, or by a substituent -W-Z in which W represents a direct bond, lower alkylene, lower alkenylene, thio-lower alkylene or oxy-lowe alkylene and Z represents cyano, carboxy or carboxy derivatized in the form of a pharmaceutically acceptable ester or amide; R² represents hydrogen, lower alkyl or aryl-lower alkyl; R³ represents hydrogen or hydroxy; R⁴ represents hydrogen, lower alkyl, aryl-lower alkyl, cycloalkyl or hydroxy-lower alkyl; pharmaceutically accept­able ester derivatives thereof in which free hydroxy groups are esterified in form of a pharmaceutically acceptable ester; pharmaceutically acceptable salts thereof; their preparation, and their use as adenosine-2 receptor agonists are disclosed.

  式 I 的化合物 其中 R 代表氢或低级烷基；R¹ 代表环烷基、环烷基-低级烷基、2-降冰片烷基、2-降冰片烷基-低级烷基、芳基、芳基-低级烷基、芳基-环烷基、9-芴基、二芳基-低级烷基或 9-芴基-低级烷基；或 R¹ 代表双环苯并融合的 5 或 6 元饱和碳环基，或苯并融合的 5 或 6 元饱和杂环基，其中含有直接连接到融合苯环上的选自氧和硫的杂原子，任何上述双环基均未被取代或在苯并部分被低级烷基取代、低级烷氧基、羟基、卤素或三氟甲基，或取代基-W-Z，其中 W 代表直接键、低级亚烷基、低级亚烯基、硫代低级亚烷基或氧代低级亚烷基，Z 代表氰基、羧基或以药学上可接受的酯或酰胺形式衍生的羧基；R²代表氢、低级烷基或芳基-低级烷基；R³代表氢或羟基；R⁴代表氢、低级烷基、芳基-低级烷基、环烷基或羟基-低级烷基；公开了其药学上可接受的酯衍生物，其中游离羟基以药学上可接受的酯的形式酯化；其药学上可接受的盐；其制备及其作为腺苷-2 受体激动剂的用途。
• US4968697A
  申请人：——

  公开号：US4968697A

  公开（公告）日：1990-11-06
• US6368573B1
  申请人：——

  公开号：US6368573B1

  公开（公告）日：2002-04-09
• 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.