5'-O-(tert-butyldimethylsilyl)-2',3'-bis-O-<(methylthio)-thiocarbonyl>adenosine | 119794-32-0

• 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: 5'-O-(tert-butyldimethylsilyl)-2',3'-bis-O-<(methylthio)-thiocarbonyl>adenosine
• 英文别名: 5'-O-(tert-butyldimethylsilyl)-2',3'-bis-O-<(methylthio)thiocarbonyl>adenosine；5'-O-(tert-butyldimethylsilyl)-2',3'-bis-O-[(methylthio)thiocarbonyl]adenosine；O-[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-methylsulfanylcarbothioyloxyoxolan-3-yl] methylsulfanylmethanethioate
• CAS: 119794-32-0
• 化学式: C₂₀H₃₁N₅O₄S₄Si
• 分子量: 561.847
• InChiKey: CJGQUGZRAHARTH-LSCFUAHRSA-N

物化性质

• 沸点：
  685.2±65.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  221
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  5'-O-(tert-butyldimethylsilyl)-2',3'-bis-O-<(methylthio)-thiocarbonyl>adenosine 在 palladium on activated charcoal 偶氮二异丁腈 、 四丁基氟化铵 、 氢气 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 25.0 ℃ 、103.42 kPa 条件下， 反应 1.67h， 生成 2',3'-双脱氧腺苷
  参考文献：
  名称：

  General syntheses of 2',3'-dideoxynucleosides and 2',3'-didehydro-2',3'-dideoxynucleosides

  摘要：

  DOI：

  10.1021/jo00270a036
• 作为产物：
  描述：

  5'-(O-tert-butyldimethylsilyl)adenosine 生成 5'-O-(tert-butyldimethylsilyl)-2',3'-bis-O-<(methylthio)-thiocarbonyl>adenosine
  参考文献：
  名称：

  CHU, C. K.;BHADTI, V. S.;DOBOSZEWSKI, B.;GU, Z. P.;KOSUGI, Y.;PULLAIAH, K+, J. ORG. CHEM., 54,(1989) N, C. 2217-2225

  摘要：

  DOI：

文献信息

• The invention of radical reactions. Part XXXI. Diphenylsilane: a reagent for deoxygenation of alcohols via their thiocarbonyl derivatives, deamination via isonitriles, and dehalogenation of bromo- and iodo- compounds by radical chain chemistry
  作者：Derek H.R. Barton、Doo Ok Jang、Joseph Cs. Jaszberenyi

  DOI：10.1016/s0040-4020(01)87198-2

  日期：1993.8

  Various thionocarbonates and xanthates of alcohols and bis-xanthates of vic-diols are readily deoxygenated to the corresponding hydrocarbons or olefins, while bromides and iodides are dehalogenated with diphenylphenylsilane in good yield.

  各种thionocarbonates和醇的黄原酸盐和二的-xanthates VIC -diols容易脱氧成相应的烃或烯烃，而溴化物和碘化物与以良好的收率diphenylphenylsilane脱卤。
• Radical deoxygenation of alcohols and intermolecular carbon–carbon bond formation with surfactant-type radical chain carriers in water
  作者：Dae Hyan Cho、Doo Ok Jang

  DOI：10.1016/j.tetlet.2005.01.107

  日期：2005.3

  An efficient and mild method is developed for radical deoxygenation of alcohols and formation of carbon–carbon bonds in water without adding additives such as surfactants. The reaction was applied to synthesis of 2′,3′-didehydro-2′,3′-dideoxynucleosides that are potent anti-HIV agents. The reaction afforded environmentally benign reaction conditions.

  开发了一种高效温和的方法，可在不添加添加剂（例如表面活性剂）的情况下对醇进行自由基脱氧并在水中形成碳-碳键。该反应用于合成有效的抗HIV药物2'，3'-didehydro-2'，3'-dideoxynucleosides。该反应提供了环境友好的反应条件。
• Radical deoxygenation of alcohols and vicinal diols with N-ethylpiperidine hypophosphite in water
  作者：Doo Ok Jang、Dae Hyan Cho

  DOI：10.1016/s0040-4039(02)01247-9

  日期：2002.8

  Radical deoxygenation of alcohols and vicinal diols with N-ethylpiperidine hypophosphite both in alcohols and in water is described. S-Methyl dithiocarbonate and bis-S-methyl dithiocarbonate of carbohydrates and nucleosides were deoxygenated efficiently under reaction conditions.

  描述了在醇和水中都用N-乙基哌啶次磷酸盐对醇和邻二醇进行自由基脱氧。小号-甲基二硫代碳酸酯和二-小号甲基碳水化合物和核苷的二硫代碳酸酯被反应条件下有效地除氧。
• The invention of radical reactions. Part XXIX. Radical mono- and dideoxygenations with silanes
  作者：Derek H.R. Barton、Doo Ok Jang、Joseph Cs. Jaszberenyi

  DOI：10.1016/s0040-4020(01)80380-x

  日期：1993.4

  Thionocarbonates and xanthates of primary and secondary alcohols, as well as bis-xanthates of vic-diols are readily deoxygenated to the corresponding hydrocarbons or olefins with phenylsilane, triphenylsilane, and triethylsilane in good yield.
• Radical mono- and dideoxygenations with the triethylsilane + benzoyl peroxide system.
  作者：Derek H.R. Barton、Doo Ok Jang、Joseph Cs. Jaszberenyi

  DOI：10.1016/0040-4039(91)80472-i

  日期：1991.12

  Thionocarbonates and xanthates of primary and secondary alcohols, as well as dixanthates of vic-diols can easily be deoxygenated to the corresponding hydrocarbons or olefins with triethylsilane and benzoyl peroxide in high-yielding radical reactions.