1-(2'-deoxy-5'-O-4,4'-dimethoxytrityl-β-D-erythro-ribofuranosyl)-2-thiouracil | 152753-91-8

• 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: 1-(2'-deoxy-5'-O-4,4'-dimethoxytrityl-β-D-erythro-ribofuranosyl)-2-thiouracil
• 英文别名: 5`-O-dimethoxytrityl-2-thio-2’-deoxy-2-thiouridine；5'-O-(4,4'-dimethoxytrityI)-2'-deoxy-2-thiouridine；1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-2-sulfanylidenepyrimidin-4-one
• CAS: 152753-91-8
• 化学式: C₃₀H₃₀N₂O₆S
• 分子量: 546.644
• InChiKey: NAUUKJXAHRJJFP-ZRRKCSAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  39
• 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：
  122
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(2'-deoxy-5'-O-4,4'-dimethoxytrityl-β-D-erythro-ribofuranosyl)-2-thiouracil 在 吡啶 、 N-甲基咪唑 、 2,4,6-三异丙基苯磺酰氯 作用下， 反应 2.63h， 生成
  参考文献：
  名称：

  A Stereoselective Synthesis of α - and β-2′-Deoxy-2-thiouridine

  摘要：

  A stereoselective glycosylation procedure is described for the synthesis of protected alpha- and beta-2'-deoxy-2-thiouridine (dS2U) in 68% and 94% yield, respectively. Evidence is presented that suggests the reaction proceeds through a silylated thioglycoside intermediate. This intermediate undergoes an efficient S2-->N1 rearrangement mediated by SnCl4. The phosphoramidite and phosphodiester synthons and a dS2U dinucleotide are also synthesized and the X-ray structure of beta-dS2U is presented.

  DOI：

  10.1080/07328319308021507
• 作为产物：
  描述：

  1-(2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-erythro-ribofuranosyl)-2-thiouracil 在 吡啶 、 4-二甲氨基吡啶 、 sodium methylate 作用下， 生成 1-(2'-deoxy-5'-O-4,4'-dimethoxytrityl-β-D-erythro-ribofuranosyl)-2-thiouracil
  参考文献：
  名称：

  将2-硫代嘧啶核苷有效脱硫为相应的4-嘧啶酮

  摘要：

  描述了制备2'-脱氧-4-嘧啶酮（dH 2 U）和2'-脱氧-5-甲基-4-嘧啶酮（dH 2 T）核苷的程序。密钥变换是通过用一个简单处理相应的2-硫代类似物的新定量脱硫米氯过苯甲酸/吡啶溶液。这些核苷的亚磷酰胺也已经合成。

  DOI：

  10.1016/s0040-4039(00)79235-5

文献信息

• Reaction of S-geranyl-2-thiouracil modified oligonucleotides with alkyl amines leads to the N2-alkyl isocytosine derivatives
  作者：Grazyna Leszczynska、Klaudia Sadowska、Malgorzata Sierant、Milena Sobczak、Barbara Nawrot、Elzbieta Sochacka

  DOI：10.1039/c7ob01012e

  日期：——

  identified very recently in bacterial tRNAs. Our study on the synthesis of geS2Ura-containing oligonucleotides (geS2U-RNA and geS2dU-DNA) revealed fast substitution of S-geranyl moiety by methylamine (frequently used in oligonucleotide deprotection procedures) or n-butylamine, providing the corresponding N2-alkyl isocytosine (R2isoCyt) derivatives. To retain the S-geranyl moiety in the DNA or RNA chains

  S-甘氨酰化2-硫尿苷（geS2Us）是细菌tRNA中最近发现的独特的疏水修饰核苷。我们对包含geS2Ura的寡核苷酸（geS2U-RNA和geS2dU-DNA）的合成研究表明，S-香叶基部分被甲胺（经常用于寡核苷酸脱保护步骤）或正丁胺快速取代，从而提供了相应的N2-烷基异胞嘧啶（ R2isoCyt）衍生物。为了将S-香叶基部分保留在DNA或RNA链中，应使用具有8 M乙醇氨的最佳脱保护方案。带有R2isoCyt杂环的低聚物（R2isoC-RNA和R2isodC-DNA）的疏水性低于相应的S2U和geS2U修饰的低聚物，而与先前报道的数据相反，geS2dU-DNA和geS2U-RNA的亲脂性明显高于亲本S2Ura寡核苷酸。热力学研究表明：（a）geS2Ura和R2isoCyt修饰的寡聚体均显示出与DNA和RNA模板相似的杂交特性，（b）R2isoCyt核碱基优先与鸟嘌呤而非DNA / DNA和RNA
• Efficient desulfurization of 2-thiopyrimidine nucleosides to the corresponding 4-pyrimidinones
  作者：Robert G. Kuimelis、Krishnan P. Nambiar

  DOI：10.1016/s0040-4039(00)79235-5

  日期：1993.6

  the preparation of 2′-deoxy-4-pyrimidone (dH2U) and 2′-deoxy-5-methyl-4-pyrimidone (dH2T) nucleosides. The key transformation is a newly quantitative desulfurization of the corresponding 2-thio analogue by a brief treatment with a m-chloroperbenzoic acid/pyridine solution. The phosphoramidites of these nucleosides have also been synthesized.

  描述了制备2'-脱氧-4-嘧啶酮（dH 2 U）和2'-脱氧-5-甲基-4-嘧啶酮（dH 2 T）核苷的程序。密钥变换是通过用一个简单处理相应的2-硫代类似物的新定量脱硫米氯过苯甲酸/吡啶溶液。这些核苷的亚磷酰胺也已经合成。
• Novel Compounds and Derivatizations of DNAs and RNAs on the Nucleobases of Pyrimidines for Function, Structure and Therapeutics
  申请人：Huang Zhen

  公开号：US20120070825A1

  公开（公告）日：2012-03-22

  Disclosed are compounds of formula (I), a derivative, or a tautomer thereof, or a pharmaceutically acceptable salt of said compound or said tautomer. Also disclosed are methods of preparing compound of formula (I), a derivative, or a tautomer thereof, or a pharmaceutically acceptable salt of said compound or said tautomer. Further disclosed are methods of conducting drug discovery and research comprises applying the compound of formula (I), a derivative, or a tautomer thereof, or a pharmaceutically acceptable salt of said compound or said tautomer in an investigation.

  本发明涉及公式（I）的化合物，其衍生物或互变异构体，或该化合物或该互变异构体的药学上可接受的盐。本发明还涉及制备公式（I）的化合物，其衍生物或互变异构体，或该化合物或该互变异构体的药学上可接受的盐的方法。本发明还涉及应用公式（I）的化合物，其衍生物或互变异构体，或该化合物或该互变异构体的药学上可接受的盐，在药物发现和研究中进行研究的方法。
• [EN] NOVEL COMPOUNDS AND DERIVATIZATION OF DNAS AND RNAS ON THE NUCLEOBASES OF PYRIMIDINES FOR FUNCTION, STRUCTURE, AND THERAPEUTICS<br/>[FR] NOUVEAUX COMPOSÉS ET DÉRIVATION D'ADN ET D'ARN SUR LES NUCLÉOBASES DE PYRIMIDINES À DES FINS DE FONCTION, DE STRUCTURE ET DE THÉRAPEUTIQUE
  申请人：SENA RES INC

  公开号：WO2010135564A3

  公开（公告）日：2011-05-05
• US8809357B2
  申请人：——

  公开号：US8809357B2

  公开（公告）日：2014-08-19