9-<3'-Deoxy-3'(R)-deuterio-β-D-2'(R)-pentofuranosyl>-adenine | 127379-11-7

• 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: 9-<3'-Deoxy-3'(R)-deuterio-β-D-2'(R)-pentofuranosyl>-adenine
• 英文别名: 9-(3-deoxy-3-(R)-deuterio-β-D-erythro-pentofuranosyl)adenine；3'-Deuterio-3'-deoxyadenosine；9-(3'-Deoxy-3'(R)-deuterio-β-D-2'(R)-pentofuranosyl)-adenine；(2R,3R,4R,5S)-2-(6-aminopurin-9-yl)-4-deuterio-5-(hydroxymethyl)oxolan-3-ol
• CAS: 127379-11-7
• 化学式: C₁₀H₁₃N₅O₃
• 分子量: 252.237
• InChiKey: OFEZSBMBBKLLBJ-DOZJLROOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 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：
  119
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  腺苷 在 Amberlite IRA-400(OH) 、 2-乙酰氧基异丁酰溴 、 溶剂黄146 作用下， 反应 1.0h， 生成 9-<3'-Deoxy-3'(R)-deuterio-β-D-2'(R)-pentofuranosyl>-adenine
  参考文献：
  名称：

  Regiospecific and stereoselective conversion of ribonucleosides to 3′-deoxynucleosides. A high yield three-stage synthesis of cordycepin from adenosine.

  摘要：

  DOI：

  10.1016/s0040-4039(00)98716-1

文献信息

• Reaction of adenine nucleosides, tosylated in the carbohydrate moiety, with lithium triethylborohydride
  作者：Piet Herdewijn

  DOI：10.1016/s0040-4020(01)89533-8

  日期：1989.1

  The reaction of lithium triethylborohydride with the 2′,3′-di-O-p-tolyl-sulphonyl derivatives of 9-/bg-D-ribofuranosyladenine, 9-β-D-arabinofuranosyl-adenine, 9-β-D-xylofuranosyladenine and 9-β-D-lyxofuranosyladenine was studied. The reaction of 2′,3′-di-O-p-tolysulphonyladenosine with LiEt3BH gave 9-(3-deoxy-β-D--pentofuranosyl)adenine. This rearrangement reaction was used for the synthesis of 9-(3

  三乙基硼氢化锂与9- / bg-D-D-呋喃核糖基腺嘌呤，9-β-D-阿拉伯呋喃糖基腺嘌呤，9-β-D-木呋喃基腺嘌呤和9的2'，3'-二-Op-甲苯基-磺酰基衍生物的反应研究了-β-D-呋喃呋喃糖基腺嘌呤。2′，3′-二-Op-甲苯磺酰腺苷与LiEt 3 BH的反应得到9-（3-脱氧-β-D-戊呋喃糖基）腺嘌呤。该重排反应用于从2'，3'，5'-三-Op-甲苯磺酰赖氨酸腺苷一步合成9-（3,5-二脱氧-β-D-戊呋喃糖基）腺嘌呤，产率为58％。
• A Convenient Preparation of 3′-Deoxyadenosine (Cordycepin) and 9-[3′(<i>R</i>)-Deuterio-β-D-2′(<i>R</i>)-pentofuranosyl]-adenine
  作者：H. Bazin、J. Chattopadhyaya

  DOI：10.1055/s-1985-31441

  日期：——

  A new procedure is described for the synthesis of 3′-deoxyadenosine and 9-[3′-deoxy-3′(R)-deuterio-β-D-2′(R)-pentofuranosyl]-adenine by lithium aluminium hydride or deuteride reduction of appropriately protected 2′,3′-anhydro-ribo-adenosine.

  通过氢化铝锂或氘还原适当保护的 2′,3′-脱氢核腺苷，描述了合成 3′-脱氧腺苷和 9-[3′-脱氧-3′(R)-deuterio-δ-D-2′(R)-pentofuranosyl]-腺嘌呤的新方法。
• 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.