2-N-(Dimethylaminomethylene)-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)guanosine | 120853-22-7

分子结构分类

有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷

中文名称

——

中文别名

——

英文名称

2-N-(Dimethylaminomethylene)-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)guanosine

英文别名

2-N-dimethylaminomethylene-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)guanosine

CAS

120853-22-7

化学式

C₂₅H₄₄N₆O₆Si₂

mdl

——

分子量

580.832

InChiKey

SQVNAKSYJCMYQC-UMCMBGNQSA-N

BEILSTEIN

——

EINECS

——

物化性质

密度：

1.28±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

3.56
重原子数：

39.0
可旋转键数：

7.0
环数：

4.0
sp3杂化的碳原子比例：

0.76
拓扑面积：

136.32
氢给体数：

2.0
氢受体数：

10.0

上下游信息

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	N,N-Dimethyl-N'-{6-oxo-9-[(2R,3R,3aR,9aR)-5,5,7,7-tetraisopropyl-3-(4-methoxy-tetrahydro-pyran-4-yloxy)-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl]-6,9-dihydro-1H-purin-2-yl}-formamidine	120853-23-8	C₃₁H₅₄N₆O₈Si₂	694.976
——	2'-O-(4-methoxytetrahydropyran-4-yl)-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)guanosine	120853-24-9	C₂₈H₄₉N₅O₈Si₂	639.897
——	2-N-dimethylaminomethylene-2'-O-<1-(2-fluorophenyl)-4-methoxypiperidin-4-yl>-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)guanosine	160905-60-2	C₃₇H₅₈FN₇O₇Si₂	788.08
——	O⁶-(2-cyanoethyl)-2'-O-(4-methoxytetrahydropyran-4-yl)-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)guanosine	120853-26-1	C₃₁H₅₂N₆O₈Si₂	692.96
——	2'-O-Allyl-2-N-(dimethylaminomethylene)-6-O-diphenylcarbonyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)guanosine	——	C₄₁H₅₇N₇O₇Si₂	816.117
——	(6aR,8R,9S,9aR)-8-(2-(((dimethylamino)methylene)amino)-6-(4-nitrophenethoxy)-9H-purin-9-yl)-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-9-yl trifluoromethanesulfonate	1355611-00-5	C₃₄H₅₀F₃N₇O₁₀SSi₂	862.044
——	(6aR,8R,9R,9aR)-8-(2-(((dimethylamino)methylene)amino)-6-(4-nitrophenethoxy)-9H-purin-9-yl)-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-9-yl trifluoromethanesulfonate	1355610-98-8	C₃₄H₅₀F₃N₇O₁₀SSi₂	862.044
——	2-N-dimethylaminomethylene-2'-O-<1-(2-fluorophenyl)-4-methoxypiperidin-4-yl>guanosine	160905-73-7	C₂₅H₃₂FN₇O₆	545.571
——	2-N-dimethylaminomethylidene-2'-O-(9-phenylxanthen-9-yl)guanosine	195247-51-9	C₃₂H₃₀N₆O₆	594.627
——	2-N-dimethylaminomethylidene-2'-O-(9-phenylxanthen-9-yl)-5'-O-(tert-butoxydiphenylsilyl)guanosine	195247-52-0	C₄₈H₄₈N₆O₇Si	849.031
——	5'-O-(tert-butyldiphenylsilyl)-2-N-dimethylaminomethylene-2'-O-<1-(2-fluorophenyl)-4-methoxypiperidin-4-yl>guanosine	160905-76-0	C₄₁H₅₀FN₇O₆Si	783.975
——	2-N-dimethylaminomethylidene-2'-O-(9-phenylxanthen-9-yl)-3'-laevulinylguanosine	195247-54-2	C₃₇H₃₆N₆O₈	692.728
——	2,4,6-Trimethyl-benzenesulfonic acid 2-amino-9-[(2R,3R,3aR,9aR)-5,5,7,7-tetraisopropyl-3-(4-methoxy-tetrahydro-pyran-4-yloxy)-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl]-9H-purin-6-yl ester	120853-25-0	C₃₇H₅₉N₅O₁₀SSi₂	822.14
——	O⁶-(2-cyanoethyl)-N²-<<(9-fluorenylmethyl)oxy>carbonyl>-2'-O-(4-methoxytetrahydropyran-4-yl)-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)guanosine	120853-27-2	C₄₆H₆₂N₆O₁₀Si₂	915.203
——	2-N-dimethylaminomethylidene-2'-O-(9-phenylxanthen-9-yl)-3'-laevulinyl-5'-O-(tert-butoxydiphenylsilyl)guanosine	195247-53-1	C₅₃H₅₄N₆O₉Si	947.132
——	2-N-dimethylaminomethylene-2'-O-<1-(2-fluorophenyl)-4-methoxypiperidin-4-yl>-3'-O-(9-phenylxanthen-9-yl)guanosine	160905-62-4	C₄₄H₄₄FN₇O₇	801.874
——	O⁶-(2-cyanoethyl)-N²-<<(9-fluorenylmethyl)oxy>carbonyl>-2'-O-(4-methoxytetrahydropyran-4-yl)guanosine	120853-28-3	C₃₄H₃₆N₆O₉	672.695
——	O⁶-(2-cyanoethyl)-5'-O-(4,4'-dimethoxytrityl)-N²-<<(9-fluorenylmethyl)oxy>carbonyl>-2'-O-(4-methoxytetrahydropyran-4-yl)guanosine	120881-22-3	C₅₅H₅₄N₆O₁₁	975.067
——	9H-fluoren-9-ylmethyl N-[9-[(2R,3R,4R,5R)-4-[benzotriazol-1-yloxy-(2-chlorophenoxy)phosphoryl]oxy-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-(4-methoxyoxan-4-yl)oxyoxolan-2-yl]-6-(2-cyanoethoxy)purin-2-yl]carbamate	120853-35-2	C₆₇H₆₁ClN₉O₁₄P	1282.7
——	N'-(9-((2R,3R,4S,5R)-3-azido-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-6-(4-nitrophenethoxy)-9H-purin-2-yl)-N,N-dimethylformimidamide	1355611-03-8	C₄₂H₄₂N₁₀O₈	814.858

反应信息

作为反应物：

描述：

2-N-(Dimethylaminomethylene)-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)guanosine 在吡啶、咪唑、均三甲苯磺酸、四丁基氟化铵作用下，以四氢呋喃、 N,N-二甲基甲酰胺、乙腈为溶剂，反应 0.13h，生成 5'-O-(tert-butyldiphenylsilyl)-2-N-dimethylaminomethylene-2'-O-<1-(2-fluorophenyl)-4-methoxypiperidin-4-yl>-3'-O-(9-phenylxanthen-9-yl)guanosine

参考文献：

名称：

Sproat, Brian S.; Beijer, Barbro; Groetli, Morten, Journal of the Chemical Society. Perkin transactions I, 1994, # 4, p. 419 - 432

摘要：

DOI：
作为产物：

描述：

鸟苷在吡啶作用下，以甲醇为溶剂，生成 2-N-(Dimethylaminomethylene)-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)guanosine

参考文献：

名称：

Sproat, Brian S.; Beijer, Barbro; Groetli, Morten, Journal of the Chemical Society. Perkin transactions I, 1994, # 4, p. 419 - 432

摘要：

DOI：

点击查看最新优质反应信息

文献信息

2′-Azido RNA, a Versatile Tool for Chemical Biology: Synthesis, X-ray Structure, siRNA Applications, Click Labeling

作者：Katja Fauster、Markus Hartl、Tobias Santner、Michaela Aigner、Christoph Kreutz、Klaus Bister、Eric Ennifar、Ronald Micura

DOI：10.1021/cb200510k

日期：2012.3.16

study includes the detailed characterization of 2′-azido nucleoside containing RNA using UV-melting profile analysis and CD and NMR spectroscopy. Importantly, the X-ray crystallographic analysis of 2′-azido uridine and 2′-azido adenosine modified RNAs reveals crucial structural details of this modification within an A-form double helical environment. The 2′-azido group supports the C3′-endo ribose conformation

化学修饰可以显着丰富核糖核酸的结构和功能库，并赋予它们新的优异性能。在这里，我们报告了新型 2'-叠氮基胞苷和 2'-叠氮基鸟苷构建块的合成，并通过掌握在叠氮基存在下使用亚磷酰胺化学的合成挑战证明它们有效的位点特异性掺入。我们的研究包括使用 UV 熔化曲线分析和 CD 和 NMR 光谱对含有 2'-叠氮基核苷的 RNA 进行详细表征。重要的是，2'-叠氮基尿苷和 2'-叠氮基腺苷修饰的 RNA 的 X 射线晶体学分析揭示了这种修饰在 A 型双螺旋环境中的关键结构细节。2'-叠氮基支持 C3'- endo核糖构象并在小沟中显示出明显的水桥氢键模式。此外，siRNA 诱导鸡成纤维细胞中脑酸溶蛋白 (BASP1) 编码基因的沉默表明，2'-叠氮基修饰在引导链中具有良好的耐受性，甚至直接在切割位点。此外，2'-叠氮基修饰与 2'-氟和/或 2'- O相容-甲基修饰以实现具有丰富修饰模式和可调特性的
Groetli, Morten; Undheim, Kjell, Acta Chemica Scandinavica, 1995, vol. 49, # 3, p. 217 - 224

作者：Groetli, Morten、Undheim, Kjell

DOI：——

日期：——
Groetli, Morten; Douglas, Mark; Beijer, Barbro, Journal of the Chemical Society. Perkin transactions I, 1997, # 18, p. 2779 - 2788

作者：Groetli, Morten、Douglas, Mark、Beijer, Barbro、Garcia, Ramon Gueimil、Eritja, Ramon、Sproat, Brian

DOI：——

日期：——
Aminoacyl derivatives of nucleosides, nucleotides, polynucleotides. 46. General synthesis of 2'(3')-O-aminoacyl oligoribonucleotides. The protection of the guanine moiety

作者：Michael D. Hagen、Stanislav Chladek

DOI：10.1021/jo00274a041

日期：1989.6
Solid-phase synthesis of branched RNA and branched DNA/RNA chimeras

作者：Morten Grøtli、Ramon Eritja、Brian Sproat

DOI：10.1016/s0040-4020(97)00731-x

日期：1997.8

An effective method for synthesising branched oligonucleotides on solid phase in the 5' to 3' direction has been developed. Special branch-point monomers enable the synthesis of branched oligonucleotides which can have sequences of different length and base composition attached to the 2'-and 3'-hydroxyl groups of the branch point ribonucleoside. The branched oligonucleotides are assembled on commercial DNA synthesisers, the crude products are readily purified by reversed phase HPLC and the fully deprotected products are conveniently analysed by mass spectrometry. (C) 1997 Elsevier Science Ltd.