2-[(2S,3R,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]acetaldehyde | 128119-39-1

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

2-[(2S,3R,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]acetaldehyde

英文别名

——

2-[(2S,3R,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]acetaldehyde化学式

CAS

128119-39-1

化学式

C₁₈H₃₀N₂O₅Si

mdl

——

分子量

382.532

InChiKey

IHVXPJRJPRRVTP-RRFJBIMHSA-N

BEILSTEIN

——

EINECS

——

物化性质

密度：

1.098±0.06 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

2.36
重原子数：

26
可旋转键数：

7
环数：

2.0
sp3杂化的碳原子比例：

0.72
拓扑面积：

84.9
氢给体数：

1
氢受体数：

5

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
——	5'-O-(tert-butyldimethylsilyl)-3'-C-allyl-2',3'-dideoxythymidine	120232-08-8	C₁₉H₃₂N₂O₄Si	380.56
——	1-[(2R,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(2,3-dihydroxy-propyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione	142325-13-1	C₁₉H₃₄N₂O₆Si	414.574
5’-O-(叔丁基二甲基甲硅烷基)胸苷	5'-tert-butyldimethylsilyloxy-2'-deoxythymidine	40733-28-6	C₁₆H₂₈N₂O₅Si	356.494
——	1-[5-O-(tert-butyldimethylsilyl)-2-deoxy-3-O-[(1-imidazolyl)thiocarbonyl]-β-D-erythro-pentofuranosyl]thymine	128119-38-0	C₂₀H₃₀N₄O₅SSi	466.634
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,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(2-hydroxy-propyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione	202722-98-3	C₁₉H₃₄N₂O₅Si	398.575
——	1-[5-O-(tert-butyldimethylsilyl)-3-C-(2-cyanoethyl)-2,3-dideoxy-β-D-erythro-pentofuranosyl]thymine	128119-41-5	C₁₈H₂₉N₃O₄Si	379.531
——	5'-O-tert-butyldimethylsilyl-3'-deoxy-3'-C-(2"-hydroxyethyl)-2"-O-(methanesulfonyl)thymidine	144944-82-1	C₁₉H₃₄N₂O₇SSi	462.64
——	[(2S,3R,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetic acid benzyl ester	291520-12-2	C₂₅H₃₆N₂O₆Si	488.656
——	1-((2R,4S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-(2-((((2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-((triethylsilyl)oxy)tetrahydrofuran-2-yl)methyl)amino)ethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione	172033-22-6	C₃₄H₅₉N₅O₈Si₂	722.042
——	[(2S,3R,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetic acid	195519-90-5	C₃₃H₃₄N₂O₈	586.642
——	[(2S,3R,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetic acid benzyl ester	380615-23-6	C₄₀H₄₀N₂O₈	676.766
——	2-[(2S,3R,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]-N-[[(2R,3S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]-N-methoxyacetamide	291520-13-3	C₅₀H₆₃N₅O₁₂Si	954.162
——	N-benzyloxy-2-[2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-N-[3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-acetamide	380615-27-0	C₅₀H₅₃N₅O₁₂	915.997

反应信息

作为反应物：

描述：

2-[(2S,3R,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]acetaldehyde 在草酰氯、二甲基亚砜、三乙胺作用下，以乙醚为溶剂，反应 4.33h，生成 1-[(2R,4R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(2-oxo-propyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

参考文献：

名称：

Butterfield, Katharine; Thomas, Eric J., Journal of the Chemical Society. Perkin transactions I, 1998, # 4, p. 737 - 745

摘要：

DOI：
作为产物：

描述：

5'-O-<(1,1-Dimethylethyl)-dimethylsilyl>-3'-O-(phenoxythioxomethyl)thymidine 在 sodium periodate 、四氧化锇作用下，以甲苯为溶剂，生成 2-[(2S,3R,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]acetaldehyde

参考文献：

名称：

AZT类似物3'-脱氧-3'-（2-丙炔基）胸苷和3'-氰甲基-3'-脱氧胸苷的合成

摘要：

描述了一种使用自由基化学方法将碳取代基引入3'-脱氧胸苷3'-位的有效方法。提出了该方法在AZT的两个紧密类似物3'-脱氧-3'-（2-丙炔基）胸苷和3'-氰甲基-3'-脱氧胸苷的合成中的应用。

DOI：

10.1016/s0040-4039(00)94577-5

点击查看最新优质反应信息

文献信息

Synthesis and biophysical studies of oligonucleotides containing hydroxamate linkages

作者：Kanda S Ramasamy、Liyan He、Vesna Stoisavljevic、Brent Harpham、Wilfried Seifert

DOI：10.1016/s0040-4039(00)00661-4

日期：2000.6

Novel oligonucleotide dimers containing hydroxamate linkages (15 and 16) were synthesized, incorporated into oligonucleotide sequences and studied for their hybridization properties with complementary DNA and RNA targets. The modified oligonucleotides showed similar binding properties and enhanced resistance to exonucleases compared to natural oligonucleotides.

合成了包含异羟肟酸酯键（15和16）的新型寡核苷酸二聚体，将其掺入寡核苷酸序列中，并研究了它们与互补DNA和RNA靶标的杂交特性。与天然寡核苷酸相比，修饰的寡核苷酸显示出相似的结合特性并增强了对核酸外切酶的抗性。
SYNTHESIS AND BIOPHYSICAL STUDIES OF OLIGONUCLEOTIDES CONTAINING HYDROXAMATE LINKAGES

作者：Kanda S. Ramasamy、Vesna Stoisavljevic、Johnson Y. N. Lau

DOI：10.1081/ncn-100002513

日期：2001.3.31

Novel thymidine dimers containing hydroxamate linkages were synthesized, incorporated into oligonucleotide sequences and studied their hybridization properties against complementary DNA and RNA targets.

合成了含有异羟肟酸酯键的新型胸苷二聚体，将其掺入寡核苷酸序列并研究了它们对互补DNA和RNA靶标的杂交特性。
Analysis of the Structure and Stability of a Backbone-Modified Oligonucleotide: Implications for Avoiding Product Inhibition in Catalytic Template-Directed Synthesis

作者：Peizhi Luo、John C. Leitzel、Zheng-Yun J. Zhan、David G. Lynn

DOI：10.1021/ja972869w

日期：1998.4.1

destabilization of a backbone-modified DNA duplex 1, formed between d(CpGpTNTpGpC), containing a single aminoethyl group (−CH2−CH2−NH2+−) in place of the phosphodiester (−O−PO2-−O−) linkage of the central TT dimer, and d(GpCpApApCpG) are investigated. Analyses for the corresponding native duplex and two other related structural analogues of duplex 1 have been compared. Duplex 1 shows a cooperative thermal melting

在 d(CpGpTNTpGpC) 之间形成的骨架修饰的 DNA 双链体 1 不稳定的结构和热力学起源，包含单个氨基乙基 (-CH2- -NH2+-) 代替磷酸二酯 (-O-PO2-- O-) 中心 TT 二聚体的连接和 d(GpCpApApCpG) 进行了研究。对相应的天然双链体和双链体 1 的两个其他相关结构类似物的分析进行了比较。双链体 1 显示了与二态过程一致的协同热熔融转变。在 2 mM 浓度下，双链体 1 的解链温度比天然双链体降低了 17 °C，这种稳定性的降低进一步归因于 7 kcal mol-1 的焓降低和熵的有利增加15 eu mol-1。核磁共振结构分析表明，修饰后的双链体 1 仍采用经典的 B-DNA 构象，并保留了 Watson-Crick 碱基配对；然而，取代修饰骨架中的天然 PO2- 基团的基团是灵活的...
Modified ollgonucleotides. Effect of 4 vs 5-atom chimeric internucleoside linkages on duplex stability

作者：Gilbert Stork、Chengzhi Zhang、Sergel Gryaznov、Ronald Schultz

DOI：10.1016/0040-4039(95)01320-h

日期：1995.9

The question whether a four or a five atom non phosphorus based internucleoside link leads to stronger binding of the resulting chimeric oligonucleotides to complementary sequences has been examined by comparing melting temperatures of relevant duplexes.
Kawai, Stephen H.; Wang, Daguang; Just, George, Canadian Journal of Chemistry, 1992, vol. 70, # 5, p. 1573 - 1580

作者：Kawai, Stephen H.、Wang, Daguang、Just, George

DOI：——

日期：——