3'-deoxy-3'-C-methylidene-5'-O-(triphenylmethyl)thymidine | 131607-35-7

• 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: 3'-deoxy-3'-C-methylidene-5'-O-(triphenylmethyl)thymidine
• 英文别名: 3'-deoxy-5'-O-trityl-3'-C-methylenethymidine；5-methyl-1-[(2R,5S)-4-methylidene-5-(trityloxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 131607-35-7
• 化学式: C₃₀H₂₈N₂O₄
• 分子量: 480.563
• InChiKey: TZYDJIGONPPXOO-KAYWLYCHSA-N

物化性质

• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3'-deoxy-3'-C-methylidene-5'-O-(triphenylmethyl)thymidine 在 四氧化锇 、 四丁基碘化铵 、 sodium hydride 、 戴斯-马丁氧化剂 、 N-甲基吗啉氧化物 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 (+)-10-camphorsulfonic acid 、 N,N-二异丙基乙胺 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 生成 (2S,3R,5R)-3-(methoxymethoxymethyl)-5-[5-methyl-2,4-dioxo-3-(phenylmethoxymethyl)pyrimidin-1-yl]-3-phenylmethoxyoxolane-2-carbaldehyde
  参考文献：
  名称：

  具有反式3,5,8-三氧杂双环[5.3.0]癸烷结构的新型桥连核酸的合成与构象

  摘要：

  成功合成了新型桥联核酸类似物2'-脱氧-反式-3'，4'-BNA胸腺嘧啶单体。从头计算和X射线结构分析，发现该反式的2'-脱氧的-融合双环[5.3.0]癸烷结构的反式-3'，4'-BNA有效约束糖褶皱用C 2 ' -远藤用适当的γ，δ和χ角度。

  DOI：

  10.1016/j.tetlet.2004.04.082
• 作为产物：
  描述：

  1-((2R,4S,5R)-4-Methanesulfonyl-5-trityloxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione 在 二溴二氟甲烷 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 1.0h， 以31%的产率得到3'-deoxy-3'-C-methylidene-5'-O-(triphenylmethyl)thymidine
  参考文献：
  名称：

  SO₂-Extrusion Reactions of Sulfonylated Nucleosides: A Novel Strategy for the Synthesis of Exocyclic Olefinic Thymidines

  摘要：

  已经从胸苷的3′-脱氧-3′-磺酰化衍生物中合成了3′-C-甲基亚烯基-2′,3′-二脱氧-5-甲基尿苷的类似物，采用了二氧化硫排出反应。

  DOI：

  10.1055/s-2008-1078265

文献信息

• NUCLEOSIDE ANALOGUES WHOSE SUGAR MOIETIES ARE BOUND IN S-FORM AND OLIGONUCLEOTIDE DERIVATIVES COMPRISING NUCLEOTIDE ANALOGUES THEREOF
  申请人：Imanishi, Takeshi

  公开号：EP1486504A1

  公开（公告）日：2004-12-15

  Compounds of the following general formula (1) and salts thereof: where A represents an alkylene group having 1 to 2 carbon atoms, etc.; B represents an aromatic heterocyclic group which may have a substituent, etc.; R1 and R2 each represent a hydrogen atom, a protective group for a hydroxyl group for synthesis of nucleic acid, a phosphate group, or -P(R4)R5 [where R4 and R5 are the same or different, and each represent a hydroxyl group, a hydroxyl group protected with a protective group for synthesis of nucleic acid, a mercapto group, a mercapto group protected with a protective group for synthesis of nucleic acid, etc.]; and R3 represents a hydrogen atom, a halogen atom, a hydroxyl group, a hydroxyl group protected with a protective group for synthesis of nucleic acid, etc. These compounds are useful for producing oligonucleotide analogues useful for the antisense method, antigene method, etc., and for producing their intermediates.

  以下通用式（1）及其盐的化合物：其中A代表具有1至2个碳原子的烷基基团等；B代表可能具有取代基的芳香杂环基团等；R1和R2分别代表氢原子，用于核酸合成的羟基保护基，磷酸基，或-P（R4）R5 [其中R4和R5相同或不同，每个代表羟基，用于核酸合成的羟基保护基，巯基，用于核酸合成的巯基保护基等]；R3代表氢原子，卤素原子，羟基，用于核酸合成的羟基保护基等。这些化合物可用于生产用于反义方法、抗基因方法等的寡核苷酸类似物，以及生产它们的中间体。
• Development of a novel nucleoside analogue with S-type sugar conformation: 2′-deoxy-trans-3′,4′-bridged nucleic acids
  作者：Tomohisa Osaki、Satoshi Obika、Yasuki Harada、Yasunori Mitsuoka、Kensaku Sugaya、Mitsuaki Sekiguchi、Somjing Roongjang、Takeshi Imanishi

  DOI：10.1016/j.tet.2007.06.040

  日期：2007.9

  4′-bridged nucleic acid (trans-3′,4′-BNA) monomers, one with a 3,5,8-trioxabicyclo[5.3.0]decane structure and the other with a 4,7-dioxabicyclo[4.3.0]nonane structure, were successfully synthesized from thymidine. The locked trans-fused ring structures of the nucleoside analogues were confirmed by X-ray crystallography, which also indicated that their furanose rings had a typical S-type conformation involving

  两个新颖的反式-3'，4'-桥联核酸（反式-3'，4'-BNA）单体，一个具有3,5,8-三氧杂双环[5.3.0]癸烷结构，另一个具有4,4由胸苷成功合成了7-二氧杂双环[4.3.0]壬烷结构。锁定反式的核苷类似物-融合环结构通过X射线晶体学，这也表示，它们的呋喃糖环有涉及℃的典型的S型构象证实'2 -内型或C 3' -外型分别糖起皱，与在DNA双链体的B型螺旋结构中观察到的环构型相同。
• Synthesis of 2′,3′-dideoxy-3′-methylene pyrimine nucleosides as potential anti-aids agents
  作者：M. Sharma、M. Bobek

  DOI：10.1016/s0040-4039(00)97972-3

  日期：1990.1

  Efficient synthesis of 2′,3′-dideoxy-3′-methylene nucleoside analogs starting from 2′-deoxy-3′-keto-nucleosides is described.

  描述了从2′-脱氧-3′-酮-核苷开始的2′，3′-二脱氧-3′-亚甲基核苷类似物的有效合成。
• Nucleoside analogues whose sugar moieties are bound in s-form and oligonucleotide derivatives comprising nucleotide analogues thereof
  申请人：Imanishi Takeshi

  公开号：US20050176941A1

  公开（公告）日：2005-08-11

  Compounds of the following general formula (1) and salts thereof: where A represents an alkylene group having 1 to 2 carbon atoms, etc.; B represents an aromatic heterocyclic group which may have a substituent, etc.; R 1 and R 2 each represent a hydrogen atom, a protective group for a hydroxyl group for synthesis of nucleic acid, a phosphate group, or —P(R 4 )R 5 [where R 4 and R 5 are the same or different, and each represent a hydroxyl group, a hydroxyl group protected with a protective group for synthesis of nucleic acid, a mercapto group, a mercapto group protected with a protective group for synthesis of nucleic acid, etc.]; and R 3 represents a hydrogen atom, a halogen atom, a hydroxyl group, a hydroxyl group protected with a protective group for synthesis of nucleic acid, etc. These compounds are useful for producing oligonucleotide analogues useful for the antisense method, antigene method, etc., and for producing their intermediates.

  以下通式（1）的化合物及其盐： 其中，A代表1至2个碳原子的烷基；B代表一种芳香杂环基团，可以具有取代基；R1和R2分别代表氢原子、用于核酸合成的羟基保护基、磷酸基或—P（R4）R5[其中，R4和R5相同或不同，每个代表羟基、用于核酸合成的羟基保护基、巯基、用于核酸合成的巯基保护基等]；R3代表氢原子、卤素原子、羟基、用于核酸合成的羟基保护基等。 这些化合物可用于制备用于反义方法、抗基因方法等的寡核苷酸类似物，以及它们的中间体。
• Adjustment of the? Dihedral Angle of an Oligonucleotide P3??N5? Phosphoramidate Enhances Its Binding Affinity towards Complementary Strands
  作者：Satoshi Obika、Mitsuaki Sekiguchi、Roongjang Somjing、Takeshi Imanishi

  DOI：10.1002/anie.200461942

  日期：2005.3.18