胸苷环-3',5'-磷酸酯 | 6453-60-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 胸苷环-3',5'-磷酸酯
• 英文名称: thymidine 3',5'-cyclic monophosphate
• 英文别名: Thymidin-cyclo-3',4'-phosphat；3',5'-cyclo-Thymidinmonophosphat；1-[(4aR,6R,7aS)-2-hydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-5-methylpyrimidine-2,4-dione
• CAS: 6453-60-7
• 化学式: C₁₀H₁₃N₂O₇P
• 分子量: 304.196
• InChiKey: QSJFDOVQWZVUQG-XLPZGREQSA-N

物化性质

• 密度：
  1.66±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  胸苷环-3',5'-磷酸酯 在 盐酸 作用下， 生成 胸腺嘧啶
  参考文献：
  名称：

  Oivanen, Mikko; Rajamaeki, Markku; Varila, Jaana, Journal of the Chemical Society. Perkin transactions II, 1994, # 2, p. 309 - 314

  摘要：

  DOI：
• 作为产物：
  描述：

  2'-Deoxythymidin-3'-monophosphat 在 potassium tert-butylate 、 氯磷酸二苯酯 作用下， 生成 胸苷环-3',5'-磷酸酯
  参考文献：
  名称：

  Novel approach to the synthesis of isotopomeric monoalkyl [¹⁶O,¹⁷O,¹⁸O]phosphates. The stereospecific one-pot conversion of (R_P)-thymidine 3′-(4-nitrophenyl)phosphorothioate into (R_P)-thymidine 3′-[¹⁶O,¹⁷O,¹⁸O]phosphate

  摘要：

  (Rp)胸苷3'-（4-硝基苯基）磷酸硫酯与苯乙烯[18O]氧化物在含[17O]水的介质中反应，以70%的产率生成(Rp)胸苷[16O,17O,18O]磷酸，其非对映异构同位素纯度不低于92%。

  DOI：

  10.1039/c39870000594

文献信息

• Phenol terminated polymers and epoxies therefrom
  申请人：The University of Akron

  公开号：US04429099A1

  公开（公告）日：1984-01-31

  The invention sets forth novel telechelic (terminally functional) prepolymers which may be reacted to form curable epoxides. On account of the incorporation of saturated elastomer chains into the prepolymers improved epoxides arise having increased moisture resistance and less brittleness than conventional epoxides. These prepolymers may be straight chain or three-armed star, emanating from a common phenyl ring nucleus. Molecular weights of the prepolymers range from about 700 to 50,000 (linear) and from about 1000 to about 75,000 (three-arm star). The epoxides are useful as coatings, in adhesives, as additives, and the like.

  本发明提出了新型末端官能化预聚物，可以反应形成可固化的环氧树脂。由于预聚物中饱和弹性体链的引入，产生了改进的环氧树脂，具有比传统环氧树脂更高的耐潮湿性和更少的脆性。这些预聚物可以是直链或三臂星形，从一个共同的苯环核发散出来。预聚物的分子量范围从约700到50,000（线性）和约1,000到约75,000（三臂星形）。环氧树脂可用于涂料、粘合剂、添加剂等方面。
• Studies on Polynucleotides. II.¹ The Synthesis and Characterization of Linear and Cyclic Thymidine Oligonucleotides²
  作者：G. M. Tener、H. G. Khorana、R. Markham、E. H. Pol

  DOI：10.1021/ja01556a017

  日期：1958.12
• Hydrolysis of the <i>cis</i>-Phenyl Ester of Thymidine 3‘,5‘-Cyclic Monophosphate:  pH-Dependent Competition between Depyrimidination and Phosphotriester Hydrolysis <i>via</i> CO and PO Bond Ruptures
  作者：Jaana Varila、Teemu Hankamäki、Mikko Oivanen、Leo H. Koole、Harri Lönnberg

  DOI：10.1021/jo960693v

  日期：1997.2.1

  Hydrolytic reactions of the cis-phenyl ester of thymidine 3',5'-cyclic monophosphate (In) have been followed by HPLC over a wide pH range. Under acidic conditions (pH < 4) two reactions compete: depyrimidination (cleavage of the N-glycosidic bond) and phosphotriester hydrolysis to a mixture of three phosphodiesters, viz. thymidine 3',5'-cyclic monophosphate (2) and thymidine 3'- and 5'-(phenyl phosphates) (3 and 4). Depyrimidination predominates (>80%) at pH < 1 and shows first-order dependence on acidity. The reaction is 4.5 to 5 times slower than with 2. The phosphotriester hydrolysis of 1a is acid catalyzed at pH < 2, giving all three phosphodiester products (2-4). Over a broad acidity range from pH 2 to 7, the reaction is pH-independent. In this pH region, the predominant product is 3 (up to 85%). At pH > 10, the hydrolysis is hydroxide-ion-catalyzed, yielding the three phosphodiester products in a 42:42:16 ratio ([2]:[3]:[4]). From pH 7 to 10, the pH-rate profile is nonlinear, possibly due to N3H deprotonation of the thymine moiety. In the same pH range, the site of bond cleavage appears to be changed. The product analyses of the corresponding methanolysis reactions suggest that the pH-independent reaction predominantly takes place via cleavage of the C5'O bond, while the alkaline reaction proceeds by rupture of one of the PO bonds. Consistent with this proposal, the pH-independent hydrolysis yields at high concentrations of sodium chloride 5'-chloro-5'-deoxythymidine 3'-(phenyl phosphate) and in concentrated acetate buffers 5'-O-acetylthymidin 3'-(phenyl phosphate). Accordingly, the hydrolytic reactions of 1a markedly differ from those of more simple 2-aryloxy-2-oxo-1,3,2-dioxaphosphorinanes.
• SOPCHIK, ALAN E.;CAIRNS, S. MATTHEW;BENTRUDE, WESLEY G., TETRAHEDRON LETT., 30,(1989) N0, C. 1221-1224
  作者：SOPCHIK, ALAN E.、CAIRNS, S. MATTHEW、BENTRUDE, WESLEY G.

  DOI：——

  日期：——
• THIO-MODIFIED APTAMER SYNTHETIC METHODS AND COMPOSITIONS
  申请人：Board of Regents,The University of Texas System

  公开号：EP1143980A1

  公开（公告）日：2001-10-17