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3',5'-di-O-acetyl-2'-deoxy-5-formyluridine | 86163-30-6

分子结构分类

有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷

中文名称

——

中文别名

——

英文名称

3',5'-di-O-acetyl-2'-deoxy-5-formyluridine

英文别名

3',5'-di-O-acetyl-5-formyl-2'-deoxyuridine；[(2R,3S,5R)-3-acetoxy-5-(5-formyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methyl acetate；[(2R,3S,5R)-3-acetyloxy-5-(5-formyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl acetate

3',5'-di-O-acetyl-2'-deoxy-5-formyluridine化学式

CAS

86163-30-6

化学式

C₁₄H₁₆N₂O₈

mdl

——

分子量

340.29

InChiKey

RWCIRYJIAIANQL-QJPTWQEYSA-N

BEILSTEIN

——

EINECS

——

物化性质

熔点：

148-150 °C(Solv: ethyl acetate (141-78-6))
密度：

1.45±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

-0.9
重原子数：

24
可旋转键数：

7
环数：

2.0
sp3杂化的碳原子比例：

0.5
拓扑面积：

128
氢给体数：

1
氢受体数：

8

上下游信息

上游原料

中文名称	英文名称	CAS号	化学式	分子量
3,5-双-O-乙酰胸苷	3',5'-diacetylthymidine	6979-97-1	C₁₄H₁₈N₂O₇	326.306
beta-胸苷	thymidine	146183-25-7	C₁₀H₁₄N₂O₅	242.232

下游产品

中文名称	英文名称	CAS号	化学式	分子量
1-((2R,4S,5R)-4-羟基-5-(羟基甲基)四氢呋喃-2-基)-2,4-二氧代-1,2,3,4-四氢嘧啶-5-甲醛	5-formyl-2'-deoxyuridine	4494-26-2	C₁₀H₁₂N₂O₆	256.215
——	(E)-5-<2-(methylthio)vinyl>-2'-deoxyuridine	86163-16-8	C₁₂H₁₆N₂O₅S	300.335
——	bis(1,2-dihydro-4-hydroxy-6-methyl-2-oxopyridin-3-yl)[1-(3,5-di-O-acetyl-2-deoxy-β-D-ribosyl)-1,2,3,4-tetrahydropyrimidin-5-yl]methane	1217597-40-4	C₂₆H₂₈N₄O₁₁	572.529
——	bis(1,2-dihydro-4-hydroxy-1,6-dimethyl-2-oxopyridin-3-yl)[1-(3,5-di-O-acetyl-2-deoxy-β-D-ribosyl)-1,2,3,4-tetrahydropyrimidin-5-yl]methane	1217597-39-1	C₂₈H₃₂N₄O₁₁	600.582
——	bis(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)[4-(3,5-di-O-acetyl-2-deoxy-β-D-ribosyl)-1,2,3,4-tetrahydropyrimidin-5-yl]methane	1190374-96-9	C₂₆H₂₆N₂O₁₃	574.498
——	[(2R,3S,5R)-3-acetyloxy-5-[2,4-dioxo-5-(4-oxo-3-phenyl-1,3-thiazolidin-2-yl)pyrimidin-1-yl]oxolan-2-yl]methyl acetate	1201671-47-7	C₂₂H₂₃N₃O₈S	489.506
——	[(2R,3S,5R)-3-acetyloxy-5-[5-[3-(4-methylphenyl)-4-oxo-1,3-thiazolidin-2-yl]-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]methyl acetate	1201671-48-8	C₂₃H₂₅N₃O₈S	503.533
——	[(2R,3S,5R)-3-acetyloxy-5-[5-[3-(4-fluorophenyl)-4-oxo-1,3-thiazolidin-2-yl]-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]methyl acetate	1201671-51-3	C₂₂H₂₂FN₃O₈S	507.496
——	[(2R,3S,5R)-3-acetyloxy-5-[5-[3-(4-bromophenyl)-4-oxo-1,3-thiazolidin-2-yl]-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]methyl acetate	1201671-49-9	C₂₂H₂₂BrN₃O₈S	568.402
——	[(2R,3S,5R)-3-acetyloxy-5-[5-[3-(4-chlorophenyl)-4-oxo-1,3-thiazolidin-2-yl]-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]methyl acetate	1201671-50-2	C₂₂H₂₂ClN₃O₈S	523.951
——	[(2R,3S,5R)-3-acetyloxy-5-[5-[3-(3-nitrophenyl)-4-oxo-1,3-thiazolidin-2-yl]-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]methyl acetate	1201671-52-4	C₂₂H₂₂N₄O₁₀S	534.503
——	5-bis(3-methyl-5-oxo-1-phenyl-4,5-dihydro-pyrazol-4-yl)methyl-1-(2-deoxy-3,5-di-O-acetylpentafuranosyl)pyrimidine-2,4(1H,3H)-dione	898225-07-5	C₃₄H₃₄N₆O₉	670.679
——	[(2R,3S,5R)-3-acetyloxy-5-[2,4-dioxo-5-(4-oxo-3-pyridin-2-yl-1,3-thiazolidin-2-yl)pyrimidin-1-yl]oxolan-2-yl]methyl acetate	1201671-53-5	C₂₁H₂₂N₄O₈S	490.494
——	5-(1H-benzo[d]imidazol-2-yl)-1-(4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione	1354943-54-6	C₁₆H₁₆N₄O₅	344.327
——	2-amino-4-[1-(3,5-di-O-acetyl-2-deoxy-β-D-ribosyl)-1,2,3,4-tetrahydropyrimidin-5-yl]-5,6-dihydro-7-methyl-5-oxo-4H-pyrano[3,2-c]pyridine-3-carbonitrile	1217597-32-4	C₂₃H₂₃N₅O₉	513.464
——	2-amino-4-[1-(3,5-di-O-acetyl-2-deoxy-β-D-ribosyl)-1,2,3,4-tetrahydropyrimidin-5-yl]-5,6-dihydro-6,7-dimethyl-5-oxo-4H-pyrano[3,2-c]pyridine-3-carbonitrile	1217597-31-3	C₂₄H₂₅N₅O₉	527.491
——	2-amino-4-[1-(3,5-di-O-acetyl-2-deoxy-β-D-ribosyl)-1,2,3,4-tetrahydropyrimidin-5-yl]-5,6-dihydro-6-ethyl-7-methyl-5-oxo-4H-pyrano[3,2-c]pyridine-3-carbonitrile	1217597-33-5	C₂₅H₂₇N₅O₉	541.517
——	2-amino-4-[1-(3,5-di-O-acetyl-2-deoxy-β-D-ribosyl)-1,2,3,4-tetrahydropyrimidin-5-yl]-4,5-dihydro-7-methyl-5-oxo-pyrano[4,3-b]pyran-3-carbonitrile	1217597-34-6	C₂₃H₂₂N₄O₁₀	514.448
——	3-(2-deoxy-β-D-ribofuranosyl)-7-methyl-3H-pyrano[2,3-d]pyrimidine-2,5-dione	1262961-82-9	C₁₃H₁₄N₂O₆	294.264

反应信息

作为反应物：

描述：

3',5'-di-O-acetyl-2'-deoxy-5-formyluridine 在三乙胺作用下，以甲醇、水为溶剂，反应 2.0h，以93%的产率得到1-((2R,4S,5R)-4-羟基-5-(羟基甲基)四氢呋喃-2-基)-2,4-二氧代-1,2,3,4-四氢嘧啶-5-甲醛

参考文献：

名称：

新型 5-取代 2'-脱氧尿苷衍生物的合成及抗病毒活性

摘要：

合成了 2'-脱氧尿苷的新 5-唑和 5-肟取代类似物。具有唑环的类似物对 Vero 细胞培养物表现出低毒性和抗疱疹活性，其中咪唑衍生物最为活跃。5-甲酰基-脱氧尿苷肟的抑制作用与含唑核苷类似物的抑制作用相当，但发现它们的细胞毒性更高；5-甲酰基脱氧尿苷的肟特别有毒。合成的核苷类似物对感染各种痘病毒变体的细胞培养物没有表现出明显的活性。

DOI：

10.1007/s11171-005-0076-7
作为产物：

描述：

3,5-双-O-乙酰胸苷在 2,6-二甲基吡啶、 sodium persulfate 、 copper(II) sulfate 作用下，反应 0.08h，生成 3',5'-di-O-acetyl-2'-deoxy-5-formyluridine

参考文献：

名称：

醛醇缩合构建的荧光核碱基类似物：5-甲酰尿嘧啶荧光标记的设计、性能和合成优化

摘要：

荧光核苷在设计用于各种生物应用的功能性核酸系统方面发挥着重要作用。因此，扩大具有独特性质的荧光核苷的应用范围已成为一项重要挑战。在此，我们报告了由 5-甲酰基嘧啶和荧光染料之间的醛醇型缩合构建的新型荧光核苷。通过反应筛选确定了两种新的荧光核碱基类似物（4a和4c），它们分别来自 2-dicyanomemethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran 和 quinolinium 部分，以及它们的光物理研究了性质和形成动力学。两者中，4a表现出独特的荧光，具有大斯托克斯位移（67-117 nm）和高环境敏感性，其粘度诱导荧光和聚集诱导发射行为证明了这一点。动力学研究表明，即使在 pH 值为 7 的水溶液中也很容易合成4a ( k obs = 6.4 × 10 -5 /s)。总体结果表明，4a是一种有前途的分子，可用于荧光核酸系统，特别是用于

DOI：

10.1002/bkcs.12534

点击查看最新优质反应信息

文献信息

Selective reduction of aldehydes and ketones to alcohols with ammonia borane in neat water

作者：Lei Shi、Yingying Liu、Qingfeng Liu、Bin Wei、Guisheng Zhang

DOI：10.1039/c2gc00006g

日期：——

Chemoselective reduction of various carbonyl compounds to alcohols with ammonia borane (AB), a nontoxic, environmentally benign, and easily handled reagent, in neat water was achieved in quantitative conversions and high isolated yields. Interestingly, α- and β-keto esters were selectively reduced to corresponding hydroxyl esters by AB, while diols were obtained when sodium borohydride was used as

化学选择性减少各种羰基化合物到酒类纯净的氨硼烷（AB），一种无毒，对环境无害且易于处理的试剂水通过定量转化和高分离收率实现了这一目标。有趣的是，α-和β-酮基酯类被AB选择性还原为相应的羟基酯，而二醇类是在什么时候获得的硼氢化钠被用作还原剂。该方法还与多种碱不稳定的保护基的存在兼容，例如甲苯磺酰，乙酰基，苯甲酰基，酯基和酸不稳定的保护基，例如三苯甲基和TBDMS基团，以及其他基团，例如不饱和双键，硝基的和氰基。最后，一公斤的反应苯甲酰甲酸酯与AB进行了水并给了扁桃酸甲酯收率达94％。
Synthesis and properties of deoxyoligonucleotides containing putrescinylthymine (nucleosides and nucleotides. LXXVI).

作者：TADAYUKI TAKEDA、KAZUYOSHI IKEDA、YOSHIHISA MIZUNO、TOHRU UEDA

DOI：10.1248/cpb.35.3558

日期：——

Putrescinylthymidine was prepared by the reduction of the Schiff base formed from a 2'-deoxy-5-formyluridine derivative and N-phthaloylputrescine, followed by deprotection. The following deoxyoligonucleotides containing putrescinylthymine (TP) were synthesized; dodecathymidylic acids containing two to four TP residues, self-complementary decanucleotides (AAGAATTCTT) and dodecanucleotides (AGATAGCTATCT) in which T residues were partly replaced by TP, and related oligomers. Oligonucleotides containing TP were resistant to nuclease S1 digestion and were poor substrates to venom phosphodiesterase. The thermal stability (Tm) of the duplex structure of oligomers containing TP was not enhanced in spite of the expected electrostatic binding between the putrescinyl and phosphoryl residues, and was rather sequence-dependent.

腐胺胸苷是通过从 2'-脱氧-5-甲酰尿苷衍生物和 N-邻苯二甲酰胺腐胺形成的希夫碱的还原反应制备的，随后进行去保护处理。合成了以下含有腐胺胸苷（TP）的脱氧寡核苷酸；含有两个到四个 TP 殘基的十二聚胸苷酸、自互补的十聚核苷酸（AAGAA TTC TT）和十二聚核苷酸（AGATAGCTATCT），其中 T 残基部分被 TP 替代，以及相关的寡聚物。含有 TP 的寡核苷酸对核酸酶 S1 消化具抵抗性，并且是毒液磷酸二酯酶的劣质底物。尽管预计腐胺和磷酸残基之间存在静电结合，含有 TP 的寡聚物双链结构的热稳定性（Tm）并没有增强，而是相当依赖序列。
Nucleosides and Nucleotides. 131. Synthesis and Properties of Oligonucleotides Containing 5-Formyl-2'-deoxyuridine.

作者：Akira ONO、Tomoko OKAMOTO、Michiyo INADA、Hiroshi NARA、Akira MATSUDA

DOI：10.1248/cpb.42.2231

日期：——

corresponding to 1 was not detected clearly by HPLC analysis of a nucleoside mixture obtained by complete hydrolysis of I-1. Therefore, the oligonucleotide I-1 was treated with cyanomethylene-triphenylphosphorane to give an oligonucleotide containing (E) and (Z)-5-(2-cyanovinyl)-2'- deoxyuridine, which was then hydrolyzed, and the newly generated nucleosides were detected by HPLC analysis. The Tm of

将胸苷转化为5-甲酰基-2'-脱氧尿苷（1），将其掺入寡核苷酸5'd（GGAGA1CTCC）3'（I-1）和5'd（GCTGC1GCGAAAGCTG）3'（II-1）。为避免副反应和降解，必须使用新开发的保护基N，N-二-（3,5-二氯苯基）乙二胺保护1的甲酰基。在用于寡核苷酸的酶完全消化的条件下，化合物1是不稳定的，因此通过HPLC分析通过I-1的完全水解获得的核苷混合物，没有清楚地检测到对应于1的峰。因此，将寡核苷酸I-1用氰基亚甲基三苯基膦处理，得到含有（E）和（Z）-5-（2-氰基乙烯基）-2'-脱氧尿苷的寡核苷酸，然后将其水解，并通过HPLC分析检测新产生的核苷。在包含0.01 M磷酸钠（pH 7.0）的缓冲液中，自我互补寡核苷酸I-1（40°C）的Tm高于亲本寡核苷酸5'd（GGAGATCTCC）3'（31°C）的Tm。）和0.1 M NaCl。在模板引物系统[引物，5'd（
Ionic liquid mediated and promoted eco-friendly preparation of thiazolidinone and pyrimidine nucleoside–thiazolidinone hybrids and their antiparasitic activities

作者：Xinying Zhang、Xiaoyan Li、Dongfang Li、Guirong Qu、Jianji Wang、Philippe M. Loiseau、Xuesen Fan

DOI：10.1016/j.bmcl.2009.09.101

日期：2009.11

acid in [bmim][PF6]. The whole procedure is simple and straightforward and no aqueous work-up is needed. By employing this protocol, a series of novel pyrimidine nucleoside–thiazolidin-4-one hybrids were prepared and their preliminary antiparasitic activities were also studied and reported.

在没有任何催化剂的情况下，通过醛，胺和巯基乙酸在[bmim] [PF 6 ]中的三组分反应，可以有效地合成2,3-二取代-1,3-噻唑烷-4-酮衍生物。整个过程简单明了，不需要水后处理。通过采用该方案，制备了一系列新型嘧啶核苷-噻唑烷-4-酮杂化物，并对其初步的抗寄生虫活性进行了研究和报道。
An Efficient Synthesis of 2-Substituted Benzoxazoles via RuCl3·3H2O Catalyzed Tandem Reactions in Ionic Liquid

作者：Xuesen Fan、Yan He、Yangyang Wang、Xinying Zhang、Jianji Wang

DOI：10.1002/cjoc.201190156

日期：2011.4

An efficient synthesis of 2‐substituted benzoxazoles through RuCl3·3H2O catalyzed, air oxidized tandem reactions of 2‐aminophenols and aldehydes in [bmim]BF4 was developed. This synthetic strategy has such advantages as mild reaction conditions, cost‐free oxidant, readily available starting materials, and recyclable catalyst and solvent. As an application, it was successfully used in the synthesis of

通过RuCl 3 ·3H 2 O催化2-氨基苯酚和醛在[bmim] BF 4中的空气氧化串联反应，可以有效合成2-取代的苯并恶唑。这种合成策略具有以下优势：反应条件温和，氧化剂成本低，原料易得，可循环使用的催化剂和溶剂。作为一种应用，它已成功用于未报告的具有潜在生物活性的5-（苯并恶唑-2-基）-2 -′-脱氧尿苷的合成。