bis(5'-thymidinyl) phosphate | 57064-85-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - （5'->5'）-二核苷酸
• 英文名称: bis(5'-thymidinyl) phosphate
• 英文别名: di(5'-thymidinyl) phosphate；TpT；thymidylyl-(5'->5')-thymidine；[5']thymidylic acid thymidin-5'-yl ester；[5']Thymidylsaeure-thymidin-5'-ylester；Thymidylyl-Thymidine；bis[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl] hydrogen phosphate
• CAS: 57064-85-4
• 化学式: C₂₀H₂₇N₄O₁₂P
• 分子量: 546.428
• InChiKey: IFAYVBVXOVCLSE-KPRKPIBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  214
• 氢给体数：
  5
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  beta-胸苷 在 四氮唑 、 2-(N,N-diisopropylamino)-2-oxo-1,3,2-oxathiaphospholane 、 叔丁基过氧化氢 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二甲基亚砜 、 癸烷 为溶剂， 反应 64.0h， 以57%的产率得到bis(5'-thymidinyl) phosphate
  参考文献：
  名称：

  Solid-Phase Synthesis of Dinucleoside and Nucleoside-Carbohydrate Phosphodiesters and Thiophosphodiesters

  摘要：

  Unprotected nucleosides (ROH) were reacted with two polymers bound to N, N-diisopropylamino- 1,3,2-oxathiaphospholane in the presence of 1H-terazole. Oxidation with tertbutyl hydroperoxide or sulfurization with Beaucage's reagent, followed by the 1,3,2-oxathiaphospholane ring opening with unprotected nucleosides or carbohydrates (R'OH) in the presence of DBU, afforded nucleoside-(5'-5')-nucleoside or nucleoside- carbohydrate phosphodiester and thiophosphodiester derivatives through the elimination of polymer-bound ethylene episulfide. This strategy offers the advantages of facile isolation of final products and monosubstitution of unprotected nucleosides and carbohydrates.

  DOI：

  10.1021/jo0611115

文献信息

• Phosphinoamidite carboxylates and analogs thereof in the synthesis of oligonucleotides having reduced internucleotide charge
  申请人：——

  公开号：US20040116687A1

  公开（公告）日：2004-06-17

  Nucleoside phosphinoamidite carboxylates and analogs are provided that have the structure of formula (III) 1 wherein A is hydrogen, hydroxyl, lower alkoxy, lower alkoxy-substituted lower alkoxy, halogen, SH, NH 2 , azide or DL wherein D is O, S or NH and L is a heteroatom-protecting group, unsubstituted hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, or substituted heteroatom-containing hydrocarbyl; B is a nucleobase; and one of R 11 and R 12 is a blocking group and the other is (IV) or (VI) 2 in which W, X, Y, Z, R 1 and n are as defined herein.

  提供了具有公式（III）结构的核苷酸磷酰胺羧酸酯和类似物，其中A为氢、羟基、低烷氧基、低烷氧基取代的低烷氧基、卤素、SH、NH2、偶氮基或DL，其中D为O、S或NH，L为杂原子保护基、未取代的烃基、取代的烃基、含杂原子的烃基或取代的含杂原子的烃基；B为核苷碱基；R11和R12中的一个是阻断基，另一个是（IV）或（VI），其中W、X、Y、Z、R1和n如此定义。
• Phosphinoamidite Carboxylates and Analogs Thereof in the Synthesis of Oligonucleotide Having Reduced Internucleotide Charge
  申请人：DELLINGER DOUGLAS J.

  公开号：US20100311960A1

  公开（公告）日：2010-12-09

  Nucleoside phosphinoamidite carboxylates and analogs are provided that have the structure of formula (III) wherein A is hydrogen, hydroxyl, lower alkoxy, lower alkoxy-substituted lower alkoxy, halogen, SH, NH 2 , azide or DL wherein D is O, S or NH and L is a heteroatom-protecting group, unsubstituted hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, or substituted heteroatom-containing hydrocarbyl; B is a nucleobase; and one of R 11 and R 12 is a blocking group and the other is (IV) or (VI) in which W, X, Y, Z, R 1 and n are as defined herein.

  提供了具有公式（III）结构的核苷酸磷酸酰胺羧酸酯和类似物，其中A是氢、羟基、较低的烷氧基、较低的烷氧基取代的较低的烷氧基、卤素、SH、NH2、偶氮基或DL，其中D是O、S或NH，L是杂原子保护基、未取代的烃基、取代的烃基、含杂原子的烃基或取代的含杂原子的烃基；B是核碱基；R11和R12中的一个是阻断基，另一个是（IV）或（VI），其中W、X、Y、Z、R1和n如本文所定义。
• Process for producing modified inorganic polymers, their use in producing polynucleotides, and a reagent useful in these processes
  申请人：UNIVERSITY PATENTS, INC.

  公开号：EP0035719A2

  公开（公告）日：1981-09-16

  Modified inorganic polymers represented by the formula wherein Ⓟ is an inorganic polymer linked to the 3' or 5' -0- of the nucleoside through a base hydrolyzable covalent bond; R is H or a blocking group; R is a hydrocarbyl radical containing up to 10 carbons; each B is a nucleoside or deoxynucleoside base; and each A is H or OR. Said inorganic polymers are chemically bound to a nucleoside. The chemical bonding of the nucleoside moiety to the inorganic polymer is by means of reactive groups on the polymer which react with reactive groups of the nucleoside molecule. Such modified inorganic polymer supports are useful in the stepwise addition of nucleosides or oligonucleotides to the original nucleoside moiety of the support by a series of process steps. The starting nucleoside which is blocked in either the 3'- or the 5'-OH and the nucleoside is coupled through the unblocked hydroxy group to the polymer support bythe coupling agent. Furthermore an automated apparatus for producing a modified silica gel which is an example of a modified inorganic polymer is shown.

  由式表示的改性无机聚合物 其中 Ⓟ是通过可水解共价键与核苷的 3'或 5'-0-相连的无机聚合物；R 是 H 或封端基；R 是含有最多 10 个碳原子的烃基；每个 B 是核苷或脱氧核苷碱基；每个 A 是 H 或 OR。所述无机聚合物与核苷进行化学键合。核苷分子与无机聚合物的化学结合是通过聚合物上的反应基团与核苷分子的反应基团进行的。这种改性的无机聚合物载体适用于通过一系列工艺步骤将核苷或寡核苷酸逐步添加到载体的原始核苷分子上。起始核苷的 3'-或 5'-羟基被阻断，核苷通过未被阻断的羟基被偶联剂偶联到聚合物载体上。此外，图中还展示了一种生产改性硅胶的自动化设备，改性硅胶是改性无机聚合物的一个例子。
• Nucleoside phosphite compounds
  申请人：UNIVERSITY PATENTS, INC.

  公开号：EP0097805A2

  公开（公告）日：1984-01-11

  New compounds of the formula wherein B is a nucleoside or deoxynucleoside base; R is H or a blocking group, A is H or OR; R, is a hydrocarbyl radical containing up to 10 carbon atoms and X is a secondary amino group. The new compounds can be chemically bound to an inorganic polymer. The chemical bonding of the nucleoside moiety to the inorganic polymer is by means of reactive groups on the polymer which react with reactive groups of the nucleoside molecule. Such modified inorganic polymer supports are useful in the stepwise addition of nucleosides or oligonucleotides to the original nucleoside moiety of the support by a series of process steps. The starting nucleoside which is blocked in either the 3'- or the 5'-OH and the nucleoside is coupled through the unblocked hydroxy group to the polymer support by the coupling agent. Furthermore an automated apparatus for producing a modified silica gel which is an example of a modified inorganic polymer is shown.

  式中的新化合物 其中 B 是核苷或脱氧核苷碱基；R 是 H 或封端基团，A 是 H 或 OR；R，是含有最多 10 个碳原子的烃基，X 是仲氨基。新化合物可与无机聚合物化学结合。核苷分子与无机聚合物的化学结合是通过聚合物上的反应基团与核苷分子的反应基团进行的。这种改性无机聚合物载体适用于通过一系列工艺步骤将核苷或寡核苷酸逐步添加到载体的原始核苷分子中。起始核苷的 3'-或 5'-羟基被阻断，核苷通过未被阻断的羟基被偶联剂偶联到聚合物载体上。此外，图中还展示了一种生产改性硅胶的自动化设备，改性硅胶是改性无机聚合物的一个例子。
• Method of synthesizing polynucleotides using ionic liquids
  申请人：——

  公开号：US20030083489A1

  公开（公告）日：2003-05-01

  A method of synthesizing polynucleotides is disclosed. The method involves contacting a first nucleotide with a selected reactive group in the presence of an ionic liquid. The selected reactive group may be on a second nucleotide, a polynucleotide, or on a moiety on an insoluble substrate, for example in an oligonucleotide synthesizer.

  本发明公开了一种合成多核苷酸的方法。该方法包括在离子液体存在下将第一核苷酸与所选反应基团接触。所选反应基团可以是第二核苷酸、多核苷酸上的，也可以是不溶性基质（例如寡核苷酸合成器）上的一个分子上的。