9-((2R,4S,5R)-4-((叔丁基二甲基硅烷基)氧基)-5-(((叔丁基二甲基硅烷基)氧基)甲基)四氢呋喃-2-基)-9H-嘌呤-6-胺 | 51549-32-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 中文名称: 9-((2R,4S,5R)-4-((叔丁基二甲基硅烷基)氧基)-5-(((叔丁基二甲基硅烷基)氧基)甲基)四氢呋喃-2-基)-9H-嘌呤-6-胺
• 英文名称: 3',5'-bis-O-[(tert-butyl)dimethylsilyl]-2'-deoxyadenosine
• 英文别名: 3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxy-adenosine；3',5'-di-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine；9-((2R,4S,5R)-4-((tert-Butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydrofuran-2-yl)-9H-purin-6-amine；9-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]purin-6-amine
• CAS: 51549-32-7
• 化学式: C₂₂H₄₁N₅O₃Si₂
• 分子量: 479.77
• InChiKey: JEDIATUHRBNRLS-GVDBMIGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.11
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  97.3
• 氢给体数：
  1
• 氢受体数：
  7

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储条件：2-8°C，避光，惰性气体保护。

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	6-azido-9-[2-deoxy-3,5-di-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]purine	1220116-30-2	C22H39N7O3Si2	505.768
  2'-脱氧腺苷	2'-Deoxyadenosine	958-09-8	C10H13N5O3	251.245
  ——	3',5'-O-bis(tert-butyldimethylsilyl)-6-N-[N-(phenylsulfonyl)carbamoyl]deoxyadenosine	909566-40-1	C29H46N6O6SSi2	662.958
  阿糖腺苷	arabinosyl adenine	5536-17-4	C10H13N5O4	267.244
  2',3'-双脱氧腺苷	2',3'-Dideoxyadenosine	4097-22-7	C10H13N5O2	235.246

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	3'-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine	51549-31-6	C16H27N5O3Si	365.508
  ——	3'-O-tert-butyldimethylsilyl-2'-deoxy-5'-O-(sylfamoyl)adenosine	862179-54-2	C16H28N6O5SSi	444.587
  ——	N6-(2-naphthyl)-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine	——	C32H47N5O3Si2	605.928
  ——	N6-(4-formylphenyl)-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine	——	C29H45N5O4Si2	583.878
  ——	3',5'-O-bis(tert-butyldimethylsilyl)-6-N-(N-phenylcarbamoyl)deoxyadenosine	——	C29H46N6O4Si2	598.893
  ——	N6-(4-methoxyphenyl)-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine	——	C29H47N5O4Si2	585.894
  ——	N6-(4-cyanophenyl)-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine	——	C29H44N6O3Si2	580.878
  ——	9-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-8-chloropurin-6-amine	116285-73-5	C22H40ClN5O3Si2	514.215
  ——	N6-(1-naphthyl)-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine	——	C32H47N5O3Si2	605.928
  ——	N6-(1-pyrenyl)-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine	577992-78-0	C38H49N5O3Si2	680.01

反应信息

• 作为反应物：
  描述：

  9-((2R,4S,5R)-4-((叔丁基二甲基硅烷基)氧基)-5-(((叔丁基二甲基硅烷基)氧基)甲基)四氢呋喃-2-基)-9H-嘌呤-6-胺 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 6.08h， 生成 N⁶-(N'-phenylcarbamoyl)-2'-deoxyadenosine
  参考文献：
  名称：

  Large Stabilization of a DNA Duplex by the Deoxyadenosine Derivatives Tethering an Aromatic Hydrocarbon Group

  摘要：

  Novel deoxyadenosine derivatives tethering a phenyl or naphthyl group by means of an amido linker have been synthesized, and these derivatives, stacking on the 5' end of a DNA duplex, provide free energy contributions equal to or greater than that of the Watson-Crick A/T base pair.

  DOI：

  10.1021/ja034465b
• 作为产物：
  描述：

  8-溴-2'-脱氧腺苷 在 咪唑 、 4-二甲氨基吡啶 、 air 、 偶氮二异丁腈 、 三(三甲基硅基)硅烷 作用下， 以 氟苯 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 9-((2R,4S,5R)-4-((叔丁基二甲基硅烷基)氧基)-5-(((叔丁基二甲基硅烷基)氧基)甲基)四氢呋喃-2-基)-9H-嘌呤-6-胺
  参考文献：
  名称：

  C5‘-Adenosinyl Radical Cyclization. A Stereochemical Investigation

  摘要：

  A variety of substituted 2'-deoxyadenosin-5'-yl radicals 3 were generated under different reaction conditions. Radicals 3 underwent intramolecular cyclization onto the C8-N7 double bond of the adenine moiety leading to aminyl radicals (5'S,8R)-4 and (5'R,8R)-4 and, eventually, to the corresponding cyclonucleosides 5 and 6. The effect of the solvent, the nature of the substituents, and the generation method of radicals 3 on the stereoselectivity of the C5'-radical cyclization have been considered. The observed increase of the (5'S)/(5'R) ratio by increasing the bulkiness of the R-1 group is explained in terms of steric repulsion between R-1 and the purine moiety which favors the C5'-endo conformation, whereas the effect of the water solvent in promoting the (5'R)-stereoselective cyclization is ascribed to intermolecular hydrogen bonding stabilizing the C5'-exo confomation.

  DOI：

  10.1021/jo060197z

文献信息

• New thermolytic carbamoyl groups for the protection of nucleobases
  作者：Akihiro Ohkubo、Rintaro Kasuya、Kenichi Miyata、Hirosuke Tsunoda、Kohji Seio、Mitsuo Sekine

  DOI：10.1039/b816831h

  日期：——

  It was found that N-arylcarbamoyl and N-(phenylsulfonyl)carbamoyl (psc) groups could be effectively introduced onto the amino groups of deoxycytidine and deoxyadenosine derivatives and could be removed thermolytically. We succeeded in synthesizing DNA probes incorporating these thermo-removable protecting groups and developed a new system for molecular switching by changing the protection- and deprotection-modes using simple heating and re-carbamoylation with isocyanates. This reversible process enabled us to control the hybridization ability of the DNA probes.

  研究发现，N-芳基氨甲酰基和N-（苯磺酰基）氨甲酰基（psc）基团能够有效地引入到脱氧胞苷和脱氧腺苷衍生物的氨基上，并且能够通过热分解反应去除。我们成功合成了含有这些热可移除保护基团的DNA探针，并开发了一种新的分子开关系统，通过简单的加热和重新氨甲酰化与异氰酸酯的反应来改变保护和脱保护模式。这种可逆的过程使我们能够控制DNA探针的杂交能力。
• Antibacterial Agents
  申请人：Aldrich Courtney

  公开号：US20080293666A1

  公开（公告）日：2008-11-27

  The invention provides compounds of formula (I) and salts thereof: R 1 -L-R 2 —B wherein R 1 , L, R 2 , and B have any of the values defined herein, as well as compositions comprising such compounds, and therapeutic methods comprising the administration of such compounds or salts. The compounds block siderophore production in bacteria and are useful as antibacterial agents.

  这项发明提供了化合物的公式(I)及其盐：R1-L-R2—B，其中R1、L、R2和B具有本文中定义的任何值，以及包含这种化合物的组合物，以及包含这种化合物或盐的治疗方法。这些化合物可以阻断细菌中的铁载体产生，并可用作抗菌剂。
• Solventless Protocol for Efficient Bis-<i>N</i>-Boc Protection of Adenosine, Cytidine, and Guanosine Derivatives
  作者：Siddharth A. Sikchi、Philip G. Hultin

  DOI：10.1021/jo060430t

  日期：2006.8.1

  A solvent-free reaction employing a simple low-energy ball mill apparatus converts the amino groups of adenosine, 2-deoxyadenosine, cytidine, 2-deoxycytidine, guanosine, and 2-deoxyguanosine as well as some of their ribosyl O-protected derivatives to the corresponding bis-N-Boc carbamates. In the case of guanosine compounds, the carbonyl group of the base moiety was also blocked as its O-Boc enol carbonate

  使用简单的低能球磨仪进行的无溶剂反应将腺苷，2-脱氧腺苷，胞嘧啶核苷，2-脱氧胞苷，鸟苷和2-脱氧鸟苷的氨基以及它们的一些核糖基O保护的衍生物转化为相应的bis- N -Boc氨基甲酸酯。在鸟苷化合物的情况下，该碱基部分的羰基也被封闭为其O- Boc烯醇碳酸酯。使用瞬态原位O硅烷化的这种方法的一种变体允许制备bis- N-Boc核苷，其中糖羟基不受保护。除鸟苷化合物外，球磨反应迅速，方便且产率很高。这种高效的方法使用适合进一步合成操作的碱稳定且酸不稳定的基团保护这些核苷的氨基。
• Caged nucleotides and oligonucleotides and their application
  申请人：——

  公开号：US08247540B2

  公开（公告）日：2012-08-21

  There is disclosed nucleotides and nucleotide analogs having a protecting or “caging” group. There is further disclosed oligonucleotides and oligonucleotides analogs formed having a protecting or “caging” group. There is further disclosed a method for decaging the nucleotides and nucleotide analogs having a protecting or “caging” group and oligonucleotides and oligonucleotide analogs having a caging group.

  披露了具有保护或“笼罩”基团的核苷酸和核苷酸类似物。进一步披露了形成具有保护或“笼罩”基团的寡核苷酸和寡核苷酸类似物。进一步披露了一种去笼罩具有保护或“笼罩”基团的核苷酸和核苷酸类似物以及具有笼罩基团的寡核苷酸和寡核苷酸类似物的方法。
• Deoxyribosyl analogues of methionyl and isoleucyl sulfamate adenylates as inhibitors of methionyl-tRNA and isoleucyl-tRNA synthetases
  作者：Sung Eun Kim、Su Yeon Kim、Sunghoon Kim、Taehee Kang、Jeewoo Lee

  DOI：10.1016/j.bmcl.2005.05.035

  日期：2005.7

  2'-Deoxy, 3'-deoxy, and 2',3'-dideoxyribosyl surrogates of isoleucyl and methionyl sulfamate adenylates have been investigated to identify the pharmacophoric importance of the ribose group for the inhibition of Escherichia coli methionyl-tRNA (MRS) and isoleucyl-tRNA (IRS) synthetases. Molecular modeling of 2',3'-dideoxyribosyl Met-NHSO2-AMP (9) with the crystal structure of E. coli MRS revealed that

  已经研究了异亮氨酰和甲硫氨酸氨基磺酸腺苷酸的2'-脱氧，3'-脱氧和2'，3'-二脱氧核糖基替代物，以鉴定核糖基团对抑制大肠杆菌甲硫氨酸-tRNA（MRS）和异亮氨酰-tRNA（IRS）合成酶。具有大肠杆菌MRS晶体结构的2'，3'-二脱氧核糖基Met-NHSO2-AMP（9）的分子模型表明，核糖之间缺少两个氢键可弥补核糖上两个羟基的缺乏环氧和His24，导致活性降低较小。