5-(hex-1-ynyl)-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione | 77875-97-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5-(hex-1-ynyl)-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
• 英文别名: 5-(1-hexyn-1-yl)-2'-deoxyuridine；5-Hex-1-ynyl-1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione；5-hex-1-ynyl-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 77875-97-9
• 化学式: C₁₅H₂₀N₂O₅
• 分子量: 308.334
• InChiKey: NWZZMQOOZLSLRJ-YNEHKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(hex-1-ynyl)-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以92%的产率得到5-(hexyl)-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Nucleic acid related compounds. 39. Efficient conversion of 5-iodo to 5-alkynyl and derived 5-substituted uracil bases and nucleosides

  摘要：

  DOI：

  10.1021/jo00159a012
• 作为产物：
  描述：

  碘苷 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 5-(hex-1-ynyl)-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Zwitterionic DNA

  摘要：

  As a strategy to make DNA net charge neutral, oligodeoxynucleotides bearing pyrimidine 5-omega-aminohexyl substituents have been synthesized and characterized. The resultant zwitterionic oligomers bind to natural DNA at low ionic strength as well or better than does natural DNA with itself, even when all of the nucleotides in a given single. strand are rendered zwitterionic. As would be expected, stabilities of duplexes bearing zwitterionic strands are relatively insensitive to changes in solution ionic strength as compared with natural DNA. Somewhat surprising, however, is the finding that a DNA duplex composed of a fully zwitterionic strand and a natural complementary strand exhibits no change in stability over a 20-fold change in ionic strength. Thus, double- and single-stranded states in this case have equivalent charge densities, consistent with the zwitterionic strand contributing no net charge. Stabilization due to the ammonium ions was verified by comparing free energies of DNA duplexes bearing hexyl tethered ammonium ions with those bearing simply hexyl groups devoid of ammonium ions. This comparison showed that without an added positive ammonium ion, the hexyl tether itself has a severe and cumulative unfavorable effect on duplex stability. Finally, zwitterionic nucleotides are found to distinguish matched from mismatched nucleotides in complementary DNA strands to a degree that rivals natural DNA.

  DOI：

  10.1021/ja00069a009

文献信息

• Nucleic acid related compounds. 31. Smooth and efficient palladium-copper catalyzed coupling of terminal alkynes with 5-iodouracil nucleosides
  作者：Morris J. Robins、Philip J. Barr

  DOI：10.1016/0040-4039(81)80115-3

  日期：1981.1

  Coupling of terminal alkynes with protected 5-iodouracil nucleosides in the presence of dichlorobis(triphenylphosphine)palladium and copper(I) iodide in triethylamine gives the corresponding 5-(alkyn-1-yl)uracil nucleosides in 72–92% yields.

  在三乙胺中存在二氯双（三苯基膦）钯和碘化铜（I）的情况下，末端炔烃与受保护的5-碘尿嘧啶核苷的偶联以72-92％的收率得到相应的5-（炔-1-基）尿嘧啶核苷。
• Efficient Sonogashira Coupling of Unprotected Halonucleosides in Aqueous Solvents Using Water-Soluble Palladium Catalysts
  作者：Joon Hyung Cho、Caitlin D. Prickett、Kevin H. Shaughnessy

  DOI：10.1002/ejoc.201000313

  日期：2010.7

  prompted the continuing development of efficient synthetic methods for their preparation. We report an efficient andenvironmentally benign Sonogashira coupling reaction for alkynylation of unprotected halonucleosides in an aqueous solvent. The combination of Pd(OAc)2, CuI, and TXPTS [trisodium tri(2,4-dimethyl-5-sulfonatophenyl)phosphane] provided an effective catalyst for the alkynylation of 8-bromopurines

  C-炔基化核苷的各种应用促进了其制备的有效合成方法的持续发展。我们报告了一种有效且对环境无害的 Sonogashira 偶联反应，用于在水性溶剂中对未受保护的卤代核苷进行炔基化。Pd(OAc)2、CuI 和 TXPTS [三(2,4-二甲基-5-磺基苯基)膦三钠] 的组合为 H2O/CH3CN 中 8-溴嘌呤和 5-碘尿苷的炔基化提供了有效的催化剂 (1 :1) 产率范围为 42 至 98 %。
• Alcynyl-5 desoxy-2′ uridines par couplages d'organozinciques acetyleniques avec l'iodo-s 0-3′, 5′-bis(trimethylsilyl) desoxyuridine, catalyses par des complexes organopalladies et de nickel
  作者：Patrice Vincent、Jean-Pierre Beaucourt、Louis Pichat

  DOI：10.1016/0040-4039(81)89015-6

  日期：1981.1

  5-Alkynyl 2′-deoxyuridines are obtained in low to modest yields by the palladium and Nickel catalyzed reaction of alkynylzinc reagents with 0-3′, 5′-bis(trimethylsilyl) deoxyuridine in T.H.F.

  通过炔基锌试剂与0-3'，5'-双（三甲基甲硅烷基）脱氧尿苷的钯和镍催化反应，可以低至中等的产率获得5-炔基2'-脱氧尿苷
• Polyamide-oligonucleotide derivatives, their preparation and use
  申请人：Uhlmann Eugen

  公开号：US20050026817A1

  公开（公告）日：2005-02-03

  Polyamide-oligonucleotide derivatives of the formula F[(DNA-Li) q (PNA-Li) r (DNA-Li) s (PNA) t ] x F′ wherein q, r, s, t are, independently of one another, zero or 1, where the total of two or more adjacent q, r, s and t≧2; x is 1 to 20; DNA is a nucleic acid such as DNA or RNA or a known derivative thereof; Li is a covalent linkage between DNA and PNA, where the covalent linkage comprises a bond or an organic radical with at least one atom from the series consisting of C, N, O or S; PNA is a polyamide structure which contains at least one nucleotide base which is different from thymine; and F and F′ are end groups and/or are linked together by a covalent bond, and the physiologically tolerated salts thereof, a process for their preparation and their use as pharmaceutical, as gene probe and as primer, are described.

  本发明涉及一种多聚酰胺-寡核苷酸衍生物，其化学式为F[(DNA-Li)q(PNA-Li)r(DNA-Li)s(PNA)t]xF'，其中q、r、s、t独立地为0或1，相邻的两个或更多q、r、s和t的总和≧2；x为1到20；DNA是核酸，例如DNA或RNA或其已知衍生物；Li是DNA和PNA之间的共价连接，其中共价连接包括具有来自C、N、O或S系列中至少一个原子的键或有机基团；PNA是含有至少一个不同于胸腺嘧啶的核苷酸碱基的多聚酰胺结构；F和F'为末端基团和/或通过共价键连接在一起，以及其生理上可耐受的盐，描述了其制备过程以及作为制药、基因探针和引物的用途。
• Modified oligonucleotides, their preparation and their use
  申请人：——

  公开号：US20030096981A1

  公开（公告）日：2003-05-22

  Modified oligonucleotides which possess at least one substituted 7-deazapurine base form more stable hybridization complexes with nucleic acids than unsubstituted analogs. They are useful as inhibitors of gene expression, as probes for detecting nucleic acids, as aids in molecular biology and as pharmaceuticals or diagnostic agents. Processes for preparing them are provided.

  具有至少一个取代的7-脱氧嘌呤碱基的修饰寡核苷酸与核酸形成的杂交复合物比未修饰的类似物更稳定。它们可用作基因表达抑制剂，用于检测核酸的探针，用于分子生物学的辅助工具以及制药品或诊断试剂。提供了制备它们的过程。