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1-<2,5-bis(O-tert-butyldimethylsilyl)-β-D-erythro-pentofuran-3-ulosyl>thymine | 117174-33-1

分子结构分类

有机化合物 - 有机杂环化合物 - 二嗪类

中文名称

——

中文别名

——

英文名称

1-<2,5-bis(O-tert-butyldimethylsilyl)-β-D-erythro-pentofuran-3-ulosyl>thymine

英文别名

1-[(2R,3S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-oxooxolan-2-yl]-5-methylpyrimidine-2,4-dione

1-<2,5-bis(O-tert-butyldimethylsilyl)-β-D-erythro-pentofuran-3-ulosyl>thymine化学式

CAS

117174-33-1

化学式

C₂₂H₄₀N₂O₆Si₂

mdl

——

分子量

484.74

InChiKey

IZBZAKTZCDFQLO-SZVBFZGTSA-N

BEILSTEIN

——

EINECS

——

物化性质

密度：

1.09±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

3.72
重原子数：

32
可旋转键数：

8
环数：

2.0
sp3杂化的碳原子比例：

0.77
拓扑面积：

94.2
氢给体数：

1
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
——	1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]thymine	117174-32-0	C₂₂H₄₂N₂O₆Si₂	486.756
5-甲基尿甙	5-Methyluridine	1463-10-1	C₁₀H₁₄N₂O₆	258.231

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	1-(2',5'-di-O-(t-butyldimethylsilyl)-3'-C-cyano-3'-deoxy-β-D-ribo-pentofuranosyl)thymine	118242-39-0	C₂₃H₄₁N₃O₅Si₂	495.767
——	1-(2',5'-di-O-(t-butyldimethylsilyl)-3'-C-cyano-3'-deoxy-β-D-xylo-pentoifuranosyl)thymine	117174-34-2	C₂₃H₄₁N₃O₅Si₂	495.767
——	1-<2,5-Di-O-(tert-butyldimethylsilyl)-3-C-ethynyl-β-D-xylo-pentofuranosyl>thymine	133634-72-7	C₂₄H₄₂N₂O₆Si₂	510.778
——	1-<2-O-(tert-Butyldimethylsilyl)-3-C-ethynyl-β-D-xylo-pentofuranosyl>thymine	133634-73-8	C₁₈H₂₈N₂O₆Si	396.516
——	1-<2-O-(tert-Butyldimethylsilyl)-3-C-ethynyl-β-D-ribo-pentofuranosyl>thymine	133634-75-0	C₁₈H₂₈N₂O₆Si	396.516
——	2',5'-bis-O-(tert-butyldimethylsilyl)-3'-deoxy-3'-dehydro-3'-(E)-(N-methyloximino)-5-methyluridine	153842-95-6	C₂₃H₄₃N₃O₆Si₂	513.782
——	1-(2',5'-bis-O-tert-butyldimethylsilyl-3'-C-acetonyl-β-D-xylofuranosyl)thymine	1327159-28-3	C₂₅H₄₆N₂O₇Si₂	542.82
——	(2R,3S,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-carbonitrile	117174-41-1	C₂₃H₄₁N₃O₆Si₂	511.766
——	(2R,3R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-carbonitrile	117174-40-0	C₂₃H₄₁N₃O₆Si₂	511.766
——	(2R,3S,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-carbonitrile	117174-40-0	C₂₃H₄₁N₃O₆Si₂	511.766
——	1-(5'-O-(t-butyldimethylsilyl)-3'-C-cyano-3'-deoxy-β-D-xylo-pentofuranosyl)thymine	117174-36-4	C₁₇H₂₇N₃O₅Si	381.504
——	1-(2'-O-(t-butyldimethylsilyl)-3'-C-cyano-3'-deoxy-β-D-ribo-pentofuranosyl)thymine	118226-04-3	C₁₇H₂₇N₃O₅Si	381.504
——	(3''-R)-1-[2',5'-bis(O-tert-butyldimethylsilyl)-3'-deoxy-β-D-xylofuranosyl]thymine-3'-spiro-2''-(3''-methoxycarbonyloxirane)	272780-79-7	C₂₅H₄₄N₂O₈Si₂	556.804
——	1-<2',5'-bis-O-(tert-butyldimethylsilyl)-3'-C-cyano-3'-O-mesyl-β-D-ribofuranosyl>thymine	141684-44-8	C₂₄H₄₃N₃O₈SSi₂	589.858
——	1-<2',5'-bis-O-(tert-butyldimethylsilyl)-3'-C-cyano-3'-O-mesyl-β-D-xylofuranosyl>thymine	141684-43-7	C₂₄H₄₃N₃O₈SSi₂	589.858
——	tert-butyl 3-((2R,3R,4S,5R)-3-((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-hydroxy-4-((S)-2-hydroxypropyl)tetrahydrofuran-2-yl)-5-methyl-2,6-dioxo-3,6-dihydropyrimidine-1(2H)-carboxylate	1327159-57-8	C₃₀H₅₆N₂O₉Si₂	644.954
——	tert-butyl 3-((2R,3R,4S,5R)-3-((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-hydroxy-4-((R)-2-hydroxypropyl)tetrahydrofuran-2-yl)-5-methyl-2,6-dioxo-3,6-dihydropyrimidine-1(2H)-carboxylate	1327159-58-9	C₃₀H₅₆N₂O₉Si₂	644.954
——	1-(2',5'-bis-O-tert-butyldimethylsilyl-3'-C-acetonyl-β-D-xylofuranosyl)-3-N-(tert-butoxycarbonyl)thymine	1327159-56-7	C₃₀H₅₄N₂O₉Si₂	642.938
——	1-(2',5'-di-O-(t-butyldimethylsilyl)-3'-C-cyano-3'-O-(phenyloxythiocarbonyl)-β-D-pentofuranosyl)thymine	118222-05-2	C₃₀H₄₅N₃O₇SSi₂	647.94
——	O-((2R,3R,4S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-cyano-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl) O-phenyl carbonothioate	118222-09-6	C₂₄H₃₁N₃O₆SSi	517.678
——	1-[(2',5'-bis-O-tert-butyldimethylsilyl-β-D-xylofuranosyl)-3-N-tert-butoxycarbonylthymine]-3'-spiro-6''-(4''-(R)-methyl-1'',3'',2''-dioxathiane-2'',2''-dioxide)	1327159-59-0	C₃₀H₅₄N₂O₁₁SSi₂	707.003
——	1-(3'-C-cyano-3'-deoxy-β-D-xylo-pentofuranosyl)thymine	117174-35-3	C₁₁H₁₃N₃O₅	267.241
1-[(5R,6R,7R,9R)-4-氨基-6-(叔丁基-二甲基硅烷基)氧基-9-[(叔丁基-二甲基硅烷基)氧基甲基]-2,2-二氧代-1,8-二氧杂-2-硫杂螺[4.4]壬-3-烯-7-基]-5-甲基嘧啶-2,4-二酮	2',5'-bis-O-(tert-butyldimethylsilyl)-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)pyrimidine	141781-17-1	C₂₄H₄₃N₃O₈SSi₂	589.858
——	<1-<2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-xylofuranosyl>thymine>-3'-spiro-5''-<4''-amino-1'',2''-oxathiole 2'',2''-dioxide>	141684-45-9	C₂₄H₄₃N₃O₈SSi₂	589.858
——	<1-<2'-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl>thymine>-3'-spiro-5''-<4''-amino-1'',2''-oxathiole 2'',2''-dioxide>	141684-47-1	C₁₈H₂₉N₃O₈SSi	475.595
——	1-(3-C-Ethynyl-β-D-xylo-pentofuranosyl)thymine	133634-74-9	C₁₂H₁₄N₂O₆	282.253
——	1-<3'-C-cyano-2',3'-dideoxy-5'-O-(t-butyldimethylsilyl)-β-D-threo-pentofuranosyl> thymine	117174-37-5	C₁₇H₂₇N₃O₄Si	365.505
——	5'-O-(t-butyldimethylsilyl)-3'-C-cyano-3'-deoxythymidine	117174-39-7	C₁₇H₂₇N₃O₄Si	365.505
——	<1-<5'-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl>thymine>-3'-spiro-5''-<4''-amino-1'',2''-oxathiole 2'',2''-dioxide>	141684-48-2	C₁₈H₂₉N₃O₈SSi	475.595
——	1-(3,5-Cyclohexylidene-3-C-ethynyl-β-D-xylo-pentofuranosyl)thymine	133634-76-1	C₁₈H₂₂N₂O₆	362.382
——	1-(2-O-Acetyl-3,5-cyclohexylidene-3-C-ethynyl-β-D-xylo-pentofuranosyl)thymine	133634-77-2	C₂₀H₂₄N₂O₇	404.42
——	<1-(β-D-ribofuranosyl)thymine>-3'-spiro-5''-<4''-amino-1'',2''-oxathiole 2'',2''-dioxide>	141781-18-2	C₁₂H₁₅N₃O₈S	361.332
——	<1-(β-D-xylofuranosyl)thymine>-3'-spiro-5''-<4''-amino-1'',2''-oxathiole 2'',2''-dioxide>	141684-46-0	C₁₂H₁₅N₃O₈S	361.332
——	<1-<5'-O-(tert-butyldimethylsilyl)-2'-deoxy-β-D-erythro-pentofuranosyl>thymine>-3'-spiro-5''-<4''-amino-1'',2''-oxathiole 2'',2''-dioxide>	141684-49-3	C₁₈H₂₉N₃O₇SSi	459.596
(2S,3R,5R)-2-(羟基甲基)-5-(5-甲基-2,4-二氧代嘧啶-1-基)四氢呋喃-3-甲腈	3'-cyano-3'-deoxythymidine	116195-58-5	C₁₁H₁₃N₃O₄	251.242
——	1-(3'-C-cyano-2',3'-dideoxy-β-D-threo-pentofuranosyl) thymine	117174-38-6	C₁₁H₁₃N₃O₄	251.242
——	5'-O-(t-butyldimethylsilyl)-3'-C-cyano-3'-deoxy-2',3'-didehydro-thymidine	118222-07-4	C₁₇H₂₅N₃O₄Si	363.489
——	1-(2',3'-dideoxy-3'-C-cyano-β-D-glyceropento-2'-enofuranosyl)thymine	118222-08-5	C₁₁H₁₁N₃O₄	249.226

反应信息

作为反应物：

描述：

1-<2,5-bis(O-tert-butyldimethylsilyl)-β-D-erythro-pentofuran-3-ulosyl>thymine 在吡啶、四丁基氟化铵、碳酸氢钠、 caesium carbonate 作用下，以乙醚、水、乙腈为溶剂，生成 <1-(β-D-ribofuranosyl)thymine>-3'-spiro-5''-<4''-amino-1'',2''-oxathiole 2'',2''-dioxide>

参考文献：

名称：

{1- [2'，5'-Bis- O-（叔丁基二甲基甲硅烷基）-β-d-二甲苯基和β-d-呋喃呋喃糖基]胸腺嘧啶} -3'-spiro-5”-{4”-的合成氨基-1″，2″-草硫醇-2″，2″-二氧化物}（TSAO）。一种新型的特异性抗HIV药物

摘要：

呋喃糖-3'-磺基胸腺嘧啶的O-甲磺酰基氰醇与碱反应，得到β-d-木糖基和核糖-3'-取代的核苷。选择性5'-O-保护的核苷的2'-脱氧得到胸苷的核呋喃糖基衍生物。

DOI：

10.1016/s0040-4039(00)79591-8
作为产物：

描述：

5-甲基尿甙在吡啶、 chromium(VI) oxide 、乙酸酐作用下，以二氯甲烷为溶剂，反应 48.75h，生成 1-<2,5-bis(O-tert-butyldimethylsilyl)-β-D-erythro-pentofuran-3-ulosyl>thymine

参考文献：

名称：

Synthesis of 3'--cyano-3'-deoxy- pentofuranosylthymine nucleosides

摘要：

DOI：

10.1016/s0040-4020(01)86194-9

点击查看最新优质反应信息

文献信息

Spiro-sulfamidate and sulfate nucleosides via 2′ and 3′-C-branched-chain sugars and nucleosides

作者：Jérôme Lalot、Tony Tite、Anne Wadouachi、Denis Postel、Albert Nguyen Van Nhien

DOI：10.1016/j.tet.2011.06.030

日期：2011.8

C-branched-chain sugars and nucleosides were obtained by organocatalysis from ulose derivatives. After a reduction step, the corresponding 1,3-diol was derivatized into 3′-spiro-sulfamidates and unexpected sulfates by treatment with a Burgess reagent. Deprotection of the Boc-derivatives was carried out while preserving the cyclic sulfate. An example of ring opening of the cyclic sulfate derivative

通过有机催化从果糖衍生物获得C-支链糖和核苷。在还原步骤之后，通过用Burgess试剂处理，将相应的1，3-二醇衍生为3'-螺氨基磺酸盐和意外的硫酸盐。在保留环状硫酸盐的同时，进行Boc衍生物的脱保护。给出了环状硫酸盐衍生物与叠氮化钠开环导致相应的3'- C-叠氮烷基支链核苷的开环的实例。
A low-temperature, photoinduced thiol–ene click reaction: a mild and efficient method for the synthesis of sugar-modified nucleosides

作者：Miklós Bege、Ilona Bereczki、Mihály Herczeg、Máté Kicsák、Dániel Eszenyi、Pál Herczegh、Anikó Borbás

DOI：10.1039/c7ob02184d

日期：——

Sugar-modified nucleosides are prime synthetic targets in anticancer and antiviral drug development. Radical mediated thiol–ene coupling was applied for the first time on nucleoside enofuranoside derivatives to produce a broad range of thio-substituted D-ribo, -arabino, -xylo and L-lyxo configured pyrimidine nucleosides. In contrast to the analogous reactions of simple sugar exomethylenes, surprisingly

糖修饰的核苷是抗癌和抗病毒药物开发中的主要合成靶标。自由基介导的硫醇-烯耦合施加首次上核苷enofuranoside衍生物，以产生宽范围的硫取代d -核糖， -阿糖， -低聚木糖和大号- L-来苏构型的嘧啶核苷。与简单的糖外亚甲基的类似反应相反，令人惊讶的是，在各种引发方法的标准条件下，核苷烯烃的氢硫醇化显示出低至中等的产率和非常低的立体选择性。优化反应条件后，我们发现冷却反应混合物对转化率和立体选择性均具有显着的有益作用，并且紫外光引发的C 2' -，C 3'-和C 2的氢硫醇化反应在-80°C时，核苷的4'-异亚甲基衍生物的产率高至高，并且在大多数情况下，其非对映异构选择性极好。在温度之外，溶剂，核苷上的保护基以及在某些情况下硫醇的构型也影响添加的立体化学结果。异常大号- L-来苏非对映选择性当加入1-硫代β-观察d -gluco-和半乳糖衍生物到Ç 4'，5'-尿苷不饱和归因于之间的空间位失配d
Synthesis of 2′- and 3′-spiro-isoxazolidine derivatives of thymidine & their conversions to 2′,3′-dideoxy-2′,3′-didehydro-3′--substituted nucleosides by radical promoted fragmentation.

作者：N. Hossain、A. Papchikhin、J. Plavec、J. Chattopadhyaya

DOI：10.1016/s0040-4020(01)80209-x

日期：1993.1

report the synthesis of a new class of 2′- and 3′-spiro-nucleosides (3 – 19, 38 – 55) by the 1,3-dipolar cycloaddition reaction of 2′- or 3′-methylnitrone (2, 36 or 37) with ethyl vinyl ether and acrylonitrile. It has been also shown that the free-radical promoted deoxygenation of 3′-hydroxy group vicinal to the 2′-spiro function in the free-radical precursor 15, 17 or 19 gives a mixture of 2′,3′-dideoxy-2′

本文我们报告了一类新的2'-和3'-螺-核苷（合成3 - 19，55 - 38通过的2'-或3'-甲基硝酮（所述1,3-偶极环加成反应）2，36或37）用乙基乙烯基醚和丙烯腈。还已经表明，3'-羟基基团邻位的在自由基前体的2'-螺功能自由基促进脱氧15，17或19给出的2' -脱氧-2 3'-混合物， '，3'-二脱氢-2' -取代的胸苷（20，21，24，26，28或32）和/或2'，3'-二脱氧-2'-螺-衍生物（30）。类似地，2'-羟基基团邻位的在自由基前体的3' -螺功能脱氧49，52或55给出的2的混合物'，3'-二脱氧-2'，3'-二脱氢-3- ' -取代的核苷（59，60或62）和/或2'，3'-二脱氧-3'-螺核苷（56和57）。本文描述的结果构成了核苷螺-（1,2-异恶唑烷）衍生物的合成及其在独特的自由基裂解反应中的应用的首次报道，以得到2'，3'-dideoxy-2'，3'
3'-Spiro nucleosides, a new class of specific human immunodeficiency virus type 1 inhibitors: synthesis and antiviral activity of [2', 5'-bis-O-(tert-butyldimethylsilyl)-.beta.-D-xylo- and -ribofuranose]-3'-spiro-5''-[4''-amino-1'', 2''-oxathiole 2'', 2''-dioxide] (TSAO) pyrimidine nucleosides

作者：Maria Jose Camarasa、Maria Jesus Perez-Perez、Ana San-Felix、Jan Balzarini、Erik De Clercq

DOI：10.1021/jm00093a002

日期：1992.7

A series of 3'-spiro nucleosides have been synthesized and evaluated as anti-HIV-1 agents. Reaction of O-mesylcyanohydrins of furanos-3'-ulosyl nucleosides with base afforded [1-[2',5'-bis-O- (tert-butyldimethylsilyl)-beta-D-xylo- and -ribofuranosyl]]-3'-spiro-5"- [4"-amino-1",2"-oxathiole 2",2"-dioxide] derivatives of thymine, uracil and 4-N-acetylcytosine 11 and 12. Desilylation of 11 and 12 gave

已经合成了一系列的3'-螺核苷，并被评估为抗HIV-1药物。呋喃糖-3'-核糖基核苷酸的O-甲磺酰基氰醇与碱反应，得到[1- [2'，5'-双-O-（叔丁基二甲基甲硅烷基）-β-D-二甲苯基和-呋喃呋喃糖基]]-3'胸腺嘧啶，尿嘧啶和4-N-乙酰胞嘧啶11和12的-spiro-5“-[4”-氨基-1“，2”-草硫醇2“，2”-二氧化物]衍生物11和12的甲硅烷基化可得到全部去保护的3'-螺木糖核糖核苷酸和核呋喃糖基核苷13和14或部分5'-O-去保护的3'-螺β-D-木糖和核糖核苷15和16，或2'-O-去保护的- 3′-螺β-D-核糖核苷17。17的2′-脱氧得到2′-脱氧-3′-螺β-D-赤型-五呋喃糖基衍生物18。这3′。评价了螺-螺衍生物的抗HIV-1活性。具有木糖构型的所有3'-螺核苷均未显示出任何抗HIV-1活性。在C-2'或C-5'处没有或仅有一个甲硅烷基或2'-脱氧衍生物的
TSAO Derivatives: Highly Specific Inhibitors of Human Immunodeficiency Virus Type-1 (HIV-1) Replication

作者：Maria Camarasa、Maria Péarez-Péarez、Sonsoles Velázquez、Ana San-Féalix、Rosa Alvarez、Simon Ingate、Maria Luisa Jimeno、Anna Karlsson、Erik De Clercq、Jan Balzarini

DOI：10.1080/15257779508012432

日期：1995.5.1

TSAO derivatives represent a unique class of nucleosides that are specifically targeted at HIV-1 RT. This overview is focussed on the chemical synthesis, the conformational studies, the antiviral and metabolic properties of TSAO derivatives, as well as their mechanism of antiviral action and the molecular basis of the vapid selection of resistant HIV-1 strains that emerge in cell culture in the presence of TSAO derivatives.