6-chloro-9-(2-deoxy-5-O-dimethoxytrityl-β-D-erythro-pentofuranosyl)purine | 133931-96-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 6-chloro-9-(2-deoxy-5-O-dimethoxytrityl-β-D-erythro-pentofuranosyl)purine
• 英文别名: 5'-O-(dimethoxytrityl)-6-chloro-2'-deoxyriboside；6-chloro-9-(2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl)purine；(6-chloro-9H-purin-9-yl)-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyriboside；(2R,3S,5R)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-5-(6-chloro-9H-purin-9-yl)tetrahydrofuran-3-ol；(2R,3S,5R)-2-[[Bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(6-chloropurin-9-yl)oxolan-3-ol
• CAS: 133931-96-1
• 化学式: C₃₁H₂₉ClN₄O₅
• 分子量: 573.048
• InChiKey: CXZJWEIBSTWESH-OYUWMTPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  41
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-chloro-9-(2-deoxy-5-O-dimethoxytrityl-β-D-erythro-pentofuranosyl)purine 在 四丁基二氟三苯硅酸铵 作用下， 以 乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 6-fluoro-9-(2-deoxy-5-O-(dimethoxytrityl)-β-D-erythro-pentofuranosyl)purine
  参考文献：
  名称：

  Utilization Of Tetrabutylammonium Triphenyldifluorosilicate (TBAT) In The Synthesis of 6-Fluoropurine Nucleosides

  摘要：

  Tetrabutylammonium triphenydifluorosilicate (TBAT) has been found to be a useful reagent for the conversion of 6-chloropurine nucleosides to 6-fluoropurine derivatives. The 6-chloropurine nucleosides were reacted with trimethylamine to form quaternary trimethylammonium salts which were treated in situ with TBAT in DMF to effect conversion to the 6-fluoro derivatives in yields of 59-72%.

  DOI：

  10.1080/07328319908044885
• 作为产物：
  描述：

  6-氯嘌呤 在 吡啶 、 N,N-二异丙基乙胺 作用下， 以 水 为溶剂， 反应 9.0h， 生成 6-chloro-9-(2-deoxy-5-O-dimethoxytrityl-β-D-erythro-pentofuranosyl)purine
  参考文献：
  名称：

  6-氯嘌呤-2'-脱氧核糖苷5'-二甲氧基三苯甲基3'-(2-氰乙基-N,N-二异丙基氨基)亚磷酰胺的半合成及其在荧光标记寡核苷酸合成中的应用

  摘要：

  在核苷-2'-脱氧核糖基转移酶 (EC 2.4.2.6) 催化下，6-氯嘌呤与 2'-脱氧胞苷反应，然后通过化学转化为 5'-二甲氧基三苯甲基 3描述了'-(2-氰乙基-N,N-二异丙基氨基)亚磷酰胺衍生物。亚磷酰胺衍生物被位点特异性地掺入寡核苷酸中，并用于引入拴系的四甲基罗丹明-尸胺偶联物。6-氯嘌呤-2'-脱氧核糖苷5'-二甲氧基三苯甲基3'-（2-氰乙基-N，N-二异丙基氨基）亚磷酰胺的有效途径的可用性使得能够轻松合成含有一系列与脱氧腺苷残基相连的官能团的寡核苷酸.

  DOI：

  10.1080/15257770.2010.530332

文献信息

• OLIGONUCLEOTIDE HAVING NON-NATURAL NUCLEOTIDE AT 5'-TERMINAL THEREOF
  申请人：Kyowa Hakko Kirin Co., Ltd.

  公开号：US20170354673A1

  公开（公告）日：2017-12-14

  An oligonucleotide having a nucleotide residue or a nucleoside residue represented by formula (I) wherein X 1 is an oxygen atom or the like, R 1 is formula (IIA) (wherein R 5A is halogen or the like, and R 6A is a hydrogen atom or the like), formula (IVA) (wherein Y 3A is a nitrogen atom or the like, and Y 4A is CH or the like), or the like, R 2 is a hydrogen atom, hydroxy, halogen, or optionally substituted lower alkoxy, and R 3 is a hydrogen atom or the like, or formula (VI) (wherein n2 is 1, 2 or 3)} at the 5′ end thereof, wherein the nucleotide residue or the nucleoside residue binds to an adjacent nucleotide residue through the oxygen atom at position 3, is provided.

  具有由式(I)表示的核苷酸残基或核苷酸残基的寡核苷酸其中X1是氧原子或类似物，R1是式(IIA)（其中R5A是卤素或类似物，而R6A是氢原子或类似物），式(IVA)（其中Y3A是氮原子或类似物，而Y4A是CH或类似物），或类似物，R2是氢原子，羟基，卤素，或可选择地取代的较低烷氧基，而R3是氢原子或类似物，或式(VI)（其中n2为1、2或3）}在其5'端，其中核苷酸残基或核苷酸残基通过位于位置3的氧原子与相邻核苷酸残基结合。
• New strategy for the synthesis of oligodeoxynucleotides bearing adducts at exocyclic amino sites of purine nucleosides
  作者：Constance M. Harris、Liang Zhou、Eric A. Strand、Thomas M. Harris

  DOI：10.1021/ja00011a044

  日期：1991.5

  stereochemical control of adduction. In this method the natural polarity of reaction, i.e., with the heterocyclic base as the nucleophilic species and the adducting moiety as electrophile, is reversed. Thus, an amino derivative of the mutagen is used to displace halogen from the appropriate halo-substituted heterocyclic species. The key to the present method is that the displacement reaction is carried

  报告一种新的低聚后策略，该策略提供了对加合物的完整区域化学和立体化学控制。在该方法中，反应的自然极性，即杂环碱作为亲核物质而加合部分作为亲电试剂被逆转。因此，诱变剂的氨基衍生物用于从合适的卤代杂环物质中置换卤素。本方法的关键是在低聚物仍附着在固体载体上时进行置换反应
• Oligonucleotide having non-natural nucleotide at 5′-terminal thereof
  申请人：Kyowa Hakko Kirin Co., Ltd.

  公开号：US10342819B2

  公开（公告）日：2019-07-09

  An oligonucleotide having a nucleotide residue or a nucleoside residue represented by formula (I) wherein X1 is an oxygen atom or the like, R1 is formula (IIA) (wherein R5A is halogen or the like, and R6A is a hydrogen atom or the like), formula (IVA) (wherein Y3A is a nitrogen atom or the like, and Y4A is CH or the like), or the like, R2 is a hydrogen atom, hydroxy, halogen, or optionally substituted lower alkoxy, and R3 is a hydrogen atom or the like, or formula (VI) (wherein n2 is 1, 2 or 3)} at the 5′ end thereof, wherein the nucleotide residue or the nucleoside residue binds to an adjacent nucleotide residue through the oxygen atom at position 3, is provided.

  具有由式(I)代表的核苷酸残基或核苷残基的寡核苷酸其中X1是氧原子或类似物，R1是式(IIA)（其中R5A是卤素或类似物，R6A是氢原子或类似物），式(IVA)（其中Y3A是氮原子或类似物，Y4A是CH或类似物），或类似物、R2是氢原子、羟基、卤素或任选取代的低级烷氧基，R3是氢原子或类似物，或式（VI）（其中n2是1、2或3）}在其5′端，其中核苷酸残基或核苷残基通过位置3的氧原子与相邻的核苷酸残基结合。
• Synthesis of Deoxyadenosine 3‘-Phosphates Bearing <i>Cis</i> and <i>Trans</i> Adducts of 7β,8α-Dihydroxy-9α,10α-epoxy-7,8,9,10-tetrahydrobenzo[<i>a</i>]pyrene:  Standards for ³²P-Postlabeling Assays
  作者：Shin Han、Constance M. Harris、Thomas M. Harris、Hye-Young Hong Kim、Seong J. Kim

  DOI：10.1021/jo9510898

  日期：1996.1.1

  Deoxyadenosine 3'-phosphates bearing cis and trans N-6 adducts of (7R) and (7S)-anti 7 beta,8 alpha-dihydroxy-9 alpha,10 alpha-epoxy-7,8,9, 10-tetrahydrobenzo[alpha]pyrenes have been prepared in good yield by reaction of 6-fluoropurinyl 2'-deoxyriboside 3'-(bis(2-[4-nitrophenyl]ethyl)phosphate with the (+/-)(7 beta,8 alpha,9 alpha,10 beta)- and (+/-)-(7 beta,8 alpha,9 alpha,10 alpha)-10-amino-7,8,9,10-tetrahydrobenzo[alpha]pyrene-7,8,9-triols. The protected phosphates are easily prepared as diasteromeric mixtures, readily resolved by reversed phase HPLC, and efficiently deprotected with DBU to give the adducted S'-phosphates. These nucleotides are of value as standards for the P-32-postlabeling procedure of Randerath for determination of benzo[alpha]pyrene adducts in DNA (Reddy et al. Carcinogenesis 1984, 5, 231).
• An Osmium−DNA Interstrand Complex:  Application to Facile DNA Methylation Analysis
  作者：Kazuo Tanaka、Kazuki Tainaka、Tadashi Umemoto、Akiko Nomura、Akimitsu Okamoto

  DOI：10.1021/ja076140r

  日期：2007.11.1

  Nucleic acids often acquire new functions by forming a variety of complexes with metal ions. Osmium, in an oxidized state, also reacts with C5-methylated pyrimidines. However, control of the sequence specificity of osmium complexation with DNA is still immature, and the value of the resulting complexes is unknown. We have designed a bipyridine-attached adenine derivative for sequence-specific osmium complexation. Sequence-specific osmium complexation was achieved by hybridization of a short DNA molecule containing this functional nucleotide to a target DNA sequence and resulted in the formation of a cross-linked structure. The interstrand cross-link clearly distinguished methylated cytosines from unmethylated cytosines and was used to quantify the degree of methylation at a specific cytosine in the genome.