[(2S,5R)-5-(2,6-二氨基嘌呤-9-基)-2,5-二氢呋喃-2-基]甲醇 | 109881-25-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: [(2S,5R)-5-(2,6-二氨基嘌呤-9-基)-2,5-二氢呋喃-2-基]甲醇
• 英文名称: 2,6-diamino-9-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)purine
• 英文别名: [(2S,5R)-5-(2,6-diaminopurin-9-yl)-2,5-dihydrofuran-2-yl]methanol
• CAS: 109881-25-6
• 化学式: C₁₀H₁₂N₆O₂
• 分子量: 248.244
• InChiKey: QVRGWJZTKCMSIW-NTSWFWBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  7

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  [(2S,5R)-5-(2,6-二氨基嘌呤-9-基)-2,5-二氢呋喃-2-基]甲醇 在 palladium on activated charcoal 甲醇 、 氢气 作用下， 以 甲醇 为溶剂， 生成 美他卡韦
  参考文献：
  名称：

  Robins, Morris J.; Wilson, John S.; Madej, Danuta, Journal of Heterocyclic Chemistry, 2001, vol. 38, # 6, p. 1297 - 1306

  摘要：

  DOI：
• 作为产物：
  描述：

  6-氯鸟嘌呤核苷 在 咪唑 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 氨 、 亚磷酸三乙酯 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 63.17h， 生成 [(2S,5R)-5-(2,6-二氨基嘌呤-9-基)-2,5-二氢呋喃-2-基]甲醇
  参考文献：
  名称：

  Robins, Morris J.; Wilson, John S.; Madej, Danuta, Journal of Heterocyclic Chemistry, 2001, vol. 38, # 6, p. 1297 - 1306

  摘要：

  DOI：

文献信息

• Synthesis of sugar-modified 2,6-diaminopurine and guanine nucleosides from guanosine via transformations of 2-aminoadenosine and enzymatic deamination with adenosine deaminase
  作者：Morris J. Robins、Ruiming Zou、Fritz Hansske、Stanislaw F. Wnuk

  DOI：10.1139/v97-092

  日期：1997.6.1

  of 2,6-diaminopurine riboside (2-aminoadenosine) with α-acetoxyisobutyryl bromide in acetonitrile gave mixtures of the trans 2′,3′-bromohydrin acetates 2. Treatment of 2 with zinc–copper couple effected reductive elimination, and deprotection gave 2,6-diamino-9-(2,3-dideoxy-β-D-erythro-pent-2-enofuranosyl)purine (3a). Treatment of 2 with Dowex 1 × 2 (OH−) resin in methanol gave the 2′,3′-anhydro derivative

  在乙腈中用 α-乙酰氧基异丁酰溴处理 2,6-二氨基嘌呤核苷（2-氨基腺苷）得到反式 2',3'-溴醇乙酸酯的混合物 2。用锌-铜对处理 2 实现还原消除，脱保护得到2,6-diamino-9-(2,3-dideoxy-β-D-erythro-pent-2-enofuranosyl)purine (3a)。在甲醇中用 Dowex 1 × 2 (OH-) 树脂处理 2 得到 2',3'-脱水衍生物 4。甲硅烷基自由基介导的 2 氢解和脱保护得到 2'-脱氧 6a 和 3'-脱氧 7a 核苷. 用三氟甲磺酰氯 - 4-（二甲氨基）吡啶处理 3',5'-O-（四异丙基二硅氧烷基）衍生物 (5a) 得到 2'-三氟甲磺酸酯 5c。用叠氮化锂-二甲基甲酰胺置换并脱保护得到阿拉伯 2'-叠氮衍生物 8a，将其还原为 2，6-diamino-9-(2-amino-2-deoxy-β-D-arabinofuranosyl)purine
• Nucleic Acid-Related Compounds. 88. Efficient Conversions of Ribonucleosides into Their 2',3'-Anhydro, 2'(and 3')-Deoxy, 2',3'-Didehydro-2',3'-dideoxy, and 2',3'-Dideoxynucleoside Analogs
  作者：Morris J. Robins、John S. Wilson、Danuta Madej、Nicholas H. Low、Fritz Hansske、Stanislaw F. Wnuk

  DOI：10.1021/jo00129a034

  日期：1995.12

  Treatment of purine, pyrimidine, and modified purine (antibiotic) ribonucleosides with 2-acetoxy-2-methylpropanoyl (alpha-acetoxyisobutyryl) bromide in acetonitrile gave mixtures of 2',3'-bromohydrin acetates with different O5' substituents. Significant amounts of 5'-unprotected (hydroxyl) bromo acetates were obtained in some cases, and formation of 2',3'-O-isopropylidene derivatives as minor byproducts was detected for the first time. Acid-catalyzed nucleophilic displacement of chloride by bromide occurred with 2-amino-6-chloropurine riboside, but no substitution of fluoride by bromide was detected with 6-amino-2-fluoropurine riboside. Treatment of the trans bromo acetate mixtures obtained from purine-type nucleosides with Dowex 1 x 2 (OH-) in methanol gave the 2',3'-anhydro (ribo epoxide) compounds. Radical-mediated hydrogenolytic debromination and deprotection gave 2'- and 3'-deoxynucleosides. Treatment of the bromo acetate mixtures with zinc-copper couple or acetic acid-activated zinc effected reductive elimination, and deprotection gave 2',3'-didehydro-2',3'-dideoxy compounds which were hydrogenated to give 2',3'-dideoxynucleosides. A number of these analogues have potent inhibitory activity against AIDS and hepatitis B viruses. New C-13 NMR data for several types of unsaturated-sugar nucleosides are tabulated. These procedures are directly applicable for the preparation of L-didehydro-dideoxy and L-dideoxy nucleoside analogues.
• Robins, Morris J.; Wilson, John S.; Madej, Danuta, Journal of Heterocyclic Chemistry, 2001, vol. 38, # 6, p. 1297 - 1306
  作者：Robins, Morris J.、Wilson, John S.、Madej, Danuta、Tyrrell, D. Lorne J.、Gati, Wendy P.、Lindmark、Wnuk, Stanislaw F.

  DOI：——

  日期：——