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1-[2-O-(tert-butyldimethylsilyl)-3-C-[(trimethylsilyl)ethynyl]-β-D-ribo-pentofuranosyl]uracil | 162611-20-3

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

1-[2-O-(tert-butyldimethylsilyl)-3-C-[(trimethylsilyl)ethynyl]-β-D-ribo-pentofuranosyl]uracil

英文别名

1-[(2R,3R,4R,5R)-3-[tert-butyl(dimethyl)silyl]oxy-4-hydroxy-5-(hydroxymethyl)-4-(2-trimethylsilylethynyl)oxolan-2-yl]pyrimidine-2,4-dione

1-[2-O-(tert-butyldimethylsilyl)-3-C-[(trimethylsilyl)ethynyl]-β-D-ribo-pentofuranosyl]uracil化学式

CAS

162611-20-3

化学式

C₂₀H₃₄N₂O₆Si₂

mdl

——

分子量

454.671

InChiKey

PIXBZZKWSRHZAU-XNWPKKHHSA-N

BEILSTEIN

——

EINECS

——

物化性质

密度：

1.18±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

辛醇/水分配系数(LogP)：

1.84
重原子数：

30
可旋转键数：

7
环数：

2.0
sp3杂化的碳原子比例：

0.7
拓扑面积：

108
氢给体数：

3
氢受体数：

6

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
——	2',5'-bis-O-tert-butyldimethylsilyl-3'-ketouridine	90813-54-0	C₂₁H₃₈N₂O₆Si₂	470.714
——	1-[2-O-(tert-butyldimethylsilyl)-β-D-erythro-pentofuran-3-ulosyl]uracil	162611-11-2	C₁₅H₂₄N₂O₆Si	356.451

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	1-[2-O-(tert-butyldimethylsilyl)-3-C-ethynyl-β-D-ribo-pentofuranosyl]uracil	399513-32-7	C₁₇H₂₆N₂O₆Si	382.489
——	3',3'-butadiynediyl-bis-[(2-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl)-uracil]	501428-34-8	C₃₄H₅₀N₄O₁₂Si₂	762.962
——	Benzoic acid (2R,3R,4R,5R)-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-5-(4-hydroxy-2-oxo-2H-pyrimidin-1-yl)-3-trimethylsilanylethynyl-tetrahydro-furan-2-ylmethyl ester	197297-89-5	C₂₇H₃₈N₂O₇Si₂	558.779
——	1-[2,5-di-O-(tert-butyldimethylsilyl)-3-C-(bromoethynyl-β-D-ribofuranosyl)]-uracil	501428-32-6	C₂₃H₃₉BrN₂O₆Si₂	575.647
——	[(2S,3S,4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-(2,4-dioxopyrimidin-1-yl)-3-(2-trimethylsilylethynyl)oxolan-2-yl]methyl benzoate	211113-82-5	C₂₇H₃₈N₂O₆Si₂	542.78
——	Benzoic acid (2S,3R,4R,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-hydroxy-2-oxo-2H-pyrimidin-1-yl)-3-trimethylsilanylethynyl-tetrahydro-furan-2-ylmethyl ester	211113-83-6	C₂₇H₃₈N₂O₆Si₂	542.78
——	Benzoic acid (2S,3S,4R,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-4-(tert-butyl-dimethyl-silanyloxy)-3-trimethylsilanylethynyl-tetrahydro-furan-2-ylmethyl ester	211113-86-9	C₂₇H₃₉N₃O₅Si₂	541.795
——	3',3'-butadiynediyl-[(2,5-di-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl)-uracil]-[(2-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl)-adenine]	501428-36-0	C₄₁H₆₅N₇O₁₀Si₃	900.264
——	Benzoic acid (2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-2H-pyrimidin-1-yl)-3-trimethylsilanylethynyl-tetrahydro-furan-2-ylmethyl ester	211113-80-3	C₂₁H₂₄N₂O₇Si	444.516
——	1-[3-C-ethynyl-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribo-pentofuranosyl]uracil	197297-97-5	C₂₃H₃₈N₂O₇Si₂	510.735
——	EUrd	180300-49-6	C₁₁H₁₂N₂O₆	268.226
——	3',3'-butadiynediyl-bis-[β-D-ribofuranosyl-uracil]	——	C₂₂H₂₂N₄O₁₂	534.436
——	Benzoic acid (3aR,4R,6R,6aR)-6-(4-hydroxy-2-oxo-2H-pyrimidin-1-yl)-2-thioxo-3a-trimethylsilanylethynyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester	1054648-13-3	C₂₂H₂₂N₂O₇SSi	486.577
——	Benzoic acid (2S,4R,5R)-4-hydroxy-5-(4-hydroxy-2-oxo-2H-pyrimidin-1-yl)-3-trimethylsilanylethynyl-tetrahydro-furan-2-ylmethyl ester	211113-81-4	C₂₁H₂₄N₂O₆Si	428.517

反应信息

作为反应物：

描述：

1-[2-O-(tert-butyldimethylsilyl)-3-C-[(trimethylsilyl)ethynyl]-β-D-ribo-pentofuranosyl]uracil 在吡啶、 potassium carbonate 作用下，以甲醇为溶剂，生成 1-[2,5-di-O-(tert-butyldimethylsilyl)-3-C-ethynyl-β-D-ribo-pentofuranosyl]uracil

参考文献：

名称：

通过向3'-β-乙炔基尿苷自由基加成苯乙烯基或巯基进行环化。3'-β-乙炔基是否是核糖核苷酸还原酶中的自旋陷阱？

摘要：

原位生成的苯乙烯基或噻吩基与AIBN在（2'-5'-二-O-叔丁基二甲基甲硅烷基-3'-C-乙炔基-β-D-呋喃呋喃糖基）尿嘧啶（2）上的反应得到60％和17％的收率分别环化了加合物3和4，其中通过向三键上加成苯乙烯基或噻吩基而形成的乙烯基与碱反应。3'-β-乙炔基尿苷二磷酸酯和三磷酸酯可能是核糖核苷酸还原酶瞬时巯基自由基的自旋阱。

DOI：

10.1016/s0040-4039(97)01308-7
作为产物：

描述：

2',5'-bis-O-tert-butyldimethylsilyl-3'-ketouridine 在正丁基锂、三氟乙酸作用下，以四氢呋喃、正己烷、水为溶剂，反应 5.5h，生成 1-[2-O-(tert-butyldimethylsilyl)-3-C-[(trimethylsilyl)ethynyl]-β-D-ribo-pentofuranosyl]uracil

参考文献：

名称：

乙炔基铈试剂的非对映选择性加成和Barton-McCombie反应是合成C-3'-乙炔基核糖核苷和C-3'-乙炔基-2'-脱氧核糖核苷的关键步骤。

摘要：

我们描述了从相应的核苷开始制备3'-炔基尿苷4a和-腺苷4b以及3'-炔基-2'-脱氧尿苷16a和-腺苷16b的方法。通过使乙炔基铈-锂试剂在3'-酮核苷上与未保护的C-5'处的羟基反应，可获得所需的C-3'叔醇立体化学。通过Barton-McCombie反应在适当的条件下进行2'-脱氧，其中在三键上抑制了氢化锡的添加。报道了对C-3'修饰的核苷的抗HIV活性的评估。

DOI：

10.1021/jo9704568

点击查看最新优质反应信息

文献信息

Nucleosides and Nucleotides. 175. Structural Requirements of the Sugar Moiety for the Antitumor Activities of New Nucleoside Antimetabolites, 1-(3-C-Ethynyl-β-<scp>d</scp>-ribo-pentofuranosyl)cytosine and -uracil

作者：Hideshi Hattori、Eisuke Nozawa、Tomoharu Iino、Yuichi Yoshimura、Satoshi Shuto、Yuji Shimamoto、Makoto Nomura、Masakazu Fukushima、Motohiro Tanaka、Takuma Sasaki、Akira Matsuda

DOI：10.1021/jm9801814

日期：1998.7.1

1-(3-C-ethynyl-beta-d-ribo-pentofuranosyl)uracil (EUrd) and its cytosine congener (ECyd) as potential multifunctional antitumor nucleoside antimetabolites. They showed potent and broad-spectrum antitumor activity against various human and mouse tumor cells in vitro and in vivo. To clarify the structure-activity relationship of the sugar moiety, various 3'-C-carbon-substituted analogues, such as 1-propynyl

我们以前设计1-（3-C-乙炔基-β-d-核糖基戊呋喃糖基）尿嘧啶（EUrd）及其胞嘧啶同源物（ECyd）作为潜在的多功能抗肿瘤核苷抗代谢物。他们在体外和体内显示出对各种人类和小鼠肿瘤细胞的有效和广谱抗肿瘤活性。为了阐明糖部分的结构-活性关系，合成了ECyd和EUrd的各种3'-C-碳取代的类似物，例如1-丙炔基，1-丁炔基，乙烯基，乙基和环丙基衍生物。我们还制备了具有不同构型的ECyd和EUrd的3'-脱氧类似物和3'-同源物，以确定3'-羟基的作用以及3'-碳原子与乙炔基之间的长度以及2'- ECyd的乙炔基衍生物可确定乙炔基的空间要求。这些核苷对小鼠白血病L1210和人KB细胞的体外肿瘤细胞生长抑制活性表明ECyd和EUrd是该系列中最有效的抑制剂，对于L1210细胞，IC50值为0.016和0.13 microM，对于L1210细胞，IC50值为0.028和0.029 microM
PREPARATION OF 1-(3-C-(PROPA-1,2-DIENYL)-D-RIBO-PENTOFURANOSYL)URACIL, AN ALLENIC NUCLEOSIDE

作者：Jérôme Dauvergne、Alain Burger、Jean-François Biellmann

DOI：10.1081/ncn-100107189

日期：2001.12.31

The Crabbé reaction was extended to the preparation of C-3′-allenyl-uridine. The effects of solvent and protecting group on the reaction were studied. The conversion in refluxing dioxan of disilyl either 3 proceeds to the corresponding allenic nucleoside 7; whereas, in refluxing THF the Mannich base 5 was obtained. Fully deprotected Mannich base and allenic uridines 6 and 9 were tested for their antitumor

Crabbé反应扩展到C-3'-烯基-尿苷的制备。研究了溶剂和保护基对反应的影响。二甲苯基中的二甲苯基在回流的二恶烷中的转化进行到相应的烯丙基核苷7; 而在回流THF中得到曼尼希碱5。测试了完全脱保护的曼尼希碱和烯丙基尿苷6和9的抗肿瘤活性。
Rapid and efficient stereocontrolled synthesis of C-3′-ethynyl ribo and xylonucleosides by organocerium additions to 3′-ketonucleosides

作者：Pierre M.J Jung、Alain Burger、Jean-Francois Biellmann

DOI：10.1016/0040-4039(94)02434-d

日期：1995.2

In order to prepare new anti-retroviral nucleoside analogues, the effect of the group at C-5' on the addition of lithium and cerium trimethylsilylacetylide on 3'-ketonucleosidcs (R(1) = H, R(1) = TBDMS) derived from adenosine and uridine was studied. The best results in respect of yield (56 to 81%) and diastereoselectivity (95:5 to >98:2) were obtained with a cerium reagent (RCcCl(2)).
Synthesis of Nucleoside Dimers Bridged on Ribose with a Butadiynyl Group

作者：Françoise Jung、Alain Burger、Jean-François Biellmann

DOI：10.1021/ol026584m

日期：2003.2.1

[GRAPHICS]The nucleoside dimer linked by a butadiynediyl group at C-3'beta may serve as a building block for the preparation of backbone-modified oligonucleotides for DNA repair or mutation in functional genomics. We prepared this type of dimer by an Eglington or Sonogashira coupling reaction. The unsymmetrical dimer was synthesized by coupling the acetylene with the bromoacetylene. Only marginal cytotoxicity was detected for one of the dimers.