1-(3-甲磺酰氧代-5-三苯代甲基氧代甲基-2-D-苏呋喃基)胸苷 | 104218-44-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 中文名称: 1-(3-甲磺酰氧代-5-三苯代甲基氧代甲基-2-D-苏呋喃基)胸苷
• 英文名称: 1-(5-O-trityl-3-O-mesyl-2-deoxy-β-D-threo-pentofuranosyl)thymine
• 英文别名: 1-(3-mesyloxy-5-trityloxymethyl-2-D-threofuryl)thymine；[(2R,3R,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-(trityloxymethyl)oxolan-3-yl] methanesulfonate
• CAS: 104218-44-2
• 化学式: C₃₀H₃₀N₂O₇S
• 分子量: 562.643
• InChiKey: NLAIOTWSOVURMN-ZONZVBGPSA-N

物化性质

• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  7

安全信息

• 安全说明：
  S61
• 危险类别码：
  R53

反应信息

• 作为反应物：
  描述：

  1-(3-甲磺酰氧代-5-三苯代甲基氧代甲基-2-D-苏呋喃基)胸苷 在 sodium azide 作用下， 以 乙二醇 为溶剂， 反应 0.75h， 以87%的产率得到3'-叠氮基-3'-脱氧-5'-O-三苯甲基胸苷
  参考文献：
  名称：

  Synthesis of 3′-N-Substituted 3′-Amino-3′-Deoxythymidine Derivatives

  摘要：

  A series of 3'-N-substituted 3'-amino-3'-deoxythymidine derivatives with alkyl, alkenyl and alkylaryl substituents was synthesized by two methods. The first method involved the reaction of 1-(2,3-dideoxy-3-O-mesyl-5-O-trityl-beta-D-threo-pentofuranosyl)thymine with an appropriate amine. In the second method, 3'-amino-5'-O-trityl-3'-deoxy-thymidine served as a synthetic precursor which was reacted with an appropiate aldehyde or ketone followed by sodium borohydride reduction. An improved synthesis of 3'-amino-3'-deoxythymidine from 3'-azido-5'-O-trityl-3'-deoxythymidine using sodium borohydride was also described.

  DOI：

  10.1080/07328319308018565
• 作为产物：
  描述：

  5'-O-tritylthymidine 在 吡啶 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 58.0h， 生成 1-(3-甲磺酰氧代-5-三苯代甲基氧代甲基-2-D-苏呋喃基)胸苷
  参考文献：
  名称：

  3'-氟-3'-脱氧胸腺嘧啶核苷的合成及其18 F-放射性标记的研究，作为无创性监测抗艾滋病药物生物分布的示踪剂

  摘要：

  3'-叠氮基胸苷（AZT）的氟化类似物3'-Fluoro-3'-脱氧胸苷（FDT）对HIV病毒更具活性，但比AZT毒性更大。由于它具有氟原子，因此可以用18 F标记，以监测该药物的生物分布和靶向性。已经开发出适用于18 F标记的FDT的新合成方法。在用三苯甲基保护5'-羟基后，将3'-羟基用Lyxo构型的甲磺酰基取代。用18 F氟化钾和Crown-18醚处理可得到18 F标记的氟代衍生物，在去三苯甲基化后可得到18 FF FDT具有7％的标记效率。这是首次报道使用氟化钾合成3'-氟-5'-O-三苯甲基脱氧胸苷并制备其18 F标记的类似物。在中间体化合物中掺入18 F并分离终产物所需的时间相当短（大约2小时），这将有足够的时间对这种短寿命的放射性核素进行生物学研究。

  DOI：

  10.1016/s0022-1139(00)82356-8

文献信息

• SO₂-Extrusion Reactions of Sulfonylated Nucleosides: A Novel Strategy for the Synthesis of Exocyclic Olefinic Thymidines
  作者：Tanmaya Pathak、Tarun Pal

  DOI：10.1055/s-2008-1078265

  日期：——

  Analogues of 3′-C-methylidene-2′,3′-dideoxy-5-meth­yluridine have been synthesized from the 3′-deoxy-3′-sulfonylated derivatives of thymidine using sulfur dioxide extrusion reaction.

  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。
• Labelling compounds for the simple synthesis of 3'-(18f)fluoro-3'-deoxy thymidine and a method for the production thereof
  申请人：——

  公开号：US20040110720A1

  公开（公告）日：2004-06-10

  The application relates to compounds that are suitable as labelable precursors for synthesis of 3′-[ 18 F]fluoro-3′-deoxythymidine and that have formula (1), 1 in which R denotes triphenylmethyl, triphenylmethyl substituted in the phenyl group, trialkylmethyl, triphenylsilyl, triphenylsilyl substituted in the phenyl group, or trialkylsilyl, R′ denotes R 1 —SO 2 , where R 1 is an unsubstituted or substituted C 1 to C 5 alkyl or an unsubstituted or substituted phenyl, and R″ denotes C 2 to C 10 alkyloxycarbonyl, with the exception of 3-N-Boc-1-(3-O-nosyl-5-O-trityl-2-deoxy-&bgr;-D-lyxofuranosyl)thymine. The application also relates to a method for preparation of these compounds and to the use of the same for synthesis of 3′-[ 18 F]fluoro-3′-deoxythymidine.

  该申请涉及适用作为可标记前体的化合物，用于合成3′-[18F]氟-3′-脱氧胸苷，并具有以下化学式（1），其中R代表三苯甲基、苯基上取代的三苯甲基、三烷基甲基、三苯基硅基、苯基上取代的三苯基硅基或三烷基硅基，R′代表R1-SO2，其中R1是未取代或取代的C1到C5烷基或未取代或取代的苯基，R″代表C2到C10烷氧羰基，除了3-N-Boc-1-(3-O-nosyl-5-O-trityl-2-deoxy-β-D-lyxofuranosyl)胸苷。该申请还涉及这些化合物的制备方法以及将其用于合成3′-[18F]氟-3′-脱氧胸苷的用途。
• Process for the deoxygenation of nucleosides
  申请人：The University of Georgia Research Foundation, Inc.

  公开号：US05384396A1

  公开（公告）日：1995-01-24

  An efficient process for the deoxygenation of 2'- and or 3'-hydroxyl groups of a nucleoside that includes reacting the hydroxyl group with 3-halopropionitrile or 2-nitroethylhalide and carbon disulfide in base to form a 2'- or 3'-(cyanoethylthio or nitroethylthio)thiocarbonyl, that is reductively eliminated and replaced with hydrogen. The deoxygenation process can be used in a wide variety of nucleoside syntheses that require the elimination of the 2'- or 3'-hydroxyl groups, including the preparation of 3'-substituted-2',3'-dideoxynucleosides such as 3'-azido-3'-deoxythymidine and 3'-azido-2',3'-dideoxyuridine.

  一种高效的去氧化核苷的过程，包括将羟基与3-卤代丙腈或2-硝基乙基卤代烷基和二硫化碳在碱性条件下反应，形成2'-或3'-(氰基乙硫或硝基乙硫)硫代羰基，然后通过还原消除并用氢取代。这种去氧化过程可用于需要消除2'-或3'-羟基的各种核苷合成，包括制备3'-取代-2',3'-二脱氧核苷，如3'-叠氮-3'-脱氧胸苷和3'-叠氮-2',3'-二脱氧尿苷。
• Synthesis and Reactions of Allenic Sulfone-Modified Thymidine: The First Allenic Sulfone to Alkylate Deoxyadenosine
  作者：Tanmaya Pathak、Sanjib Bera

  DOI：10.1055/s-2004-832807

  日期：——

  3′-(S)-(allenic sulfonyl)-5′-benzoyl-3′-deoxythymidine has been synthesized from 1-(5-O-trityl-3-O-mesyl-2-deoxy-β-d-threopentofuranosyl) thymine via 3′-(S)-(propargylthio)-5′-trityl-3′-deoxythymidine in six steps. 3′-(S)-(allenic sulfonyl)-3′-deoxy­thymidine reacts very efficiently with a wide array of nucleophiles. This is also the first report on the alkylation of adenine moiety by some allenic sulfone modified compounds.

  3′-(S)-(异烯磺酰基)-5′-苯甲酰基-3′-脱氧胸苷是由 1-(5-O-三苯甲基-3-O-甲砜基-2-脱氧-δ-d-苏氨酰)胸腺嘧啶通过 3′-(S)-(丙炔硫基)-5′-三苯甲基-3′-脱氧胸苷合成的。3′-(S)-(丙炔基硫基)-5′-三苯甲基-3′-脱氧胸苷经六个步骤由 1-(5-O-三苯甲基-3-O-甲磺酰-2-脱氧-δ-d-苏氨戊呋糖基)胸腺嘧啶合成。3′-(S)-(异戊烯磺酰基)-3′-脱氧胸苷能与多种亲核物发生高效反应。这也是首次报道一些异烯砜修饰化合物对腺嘌呤分子的烷基化作用。
• Synthesis of chemically reactive analogues of AZT and their biological evaluation against HIV
  作者：Stuart L. Schreiber、Norihiro Ikemoto

  DOI：10.1016/0040-4039(88)85124-4

  日期：1988.1

  Several 3'-deoxythymidine analogues were prepared and tested against HIV. The choice of analogues was based on their possible covalent binding to the enzyme reverse transcriptase.

  制备了几种3'-脱氧胸苷类似物，并针对HIV进行了测试。类似物的选择基于它们与酶逆转录酶的可能共价结合。