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1-[(2R,4S,5R)-4-(tert-butyldiphenylsilanyloxy)-5-hydroxymethyltetrahydrofuran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione | 83467-48-5

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-[(2R,4S,5R)-4-(tert-butyldiphenylsilanyloxy)-5-hydroxymethyltetrahydrofuran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

英文别名

1-((2R,4S,5R)-4-((tert-butyldiphenylsilyl)oxy)-5(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)dione；3'-O-tert-butyldiphenylsilyl-2'-deoxythymidine；3'-O-(tert-butyldiphenylsilyl)thymidine；3'-O-(t-butyldiphenylsilyl)thymidine；3'-O-t-butyldiphenylsilylthymidine；3'-O-TBDPS-thymidine；3'-o-t-Butyldiphenylsilyl-thymidine；1-[(2R,4S,5R)-4-[tert-butyl(diphenyl)silyl]oxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione

1-[(2R,4S,5R)-4-(tert-butyldiphenylsilanyloxy)-5-hydroxymethyltetrahydrofuran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione化学式

CAS

83467-48-5

化学式

C₂₆H₃₂N₂O₅Si

mdl

——

分子量

480.636

InChiKey

HEHSUGMKUBTCGE-YTFSRNRJSA-N

BEILSTEIN

——

EINECS

——

物化性质

熔点：

68-72 °C
密度：

1.23±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

2.07
重原子数：

34
可旋转键数：

7
环数：

4.0
sp3杂化的碳原子比例：

0.38
拓扑面积：

88.1
氢给体数：

2
氢受体数：

5

制备方法与用途

3'-O-(叔丁基二苯基甲硅烷基)胸苷是一种嘌呤核苷类似物，具有广泛的抗肿瘤活性，尤其针对惰性淋巴系统恶性肿瘤。其抗癌机制主要依赖于抑制DNA合成和诱导细胞凋亡。

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'-TBDPS-5'-p-Tol-thymidine	197719-60-1	C₃₄H₃₈N₂O₆Si	598.771
——	1-[(2R,4S,5R)-5-[bis(4-methoxyphenyl)phenylmethoxymethyl]-4-(tert-butyldiphenylsilanyloxy)tetrahydrofuran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione	198267-31-1	C₄₆H₄₈N₂O₆Si	752.982
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
beta-胸苷	thymidine	146183-25-7	C₁₀H₁₄N₂O₅	242.232
——	O^5'-(4-methyl-benzoyl)-thymidine	35898-26-1	C₁₈H₂₀N₂O₆	360.367
——	5'-O-tritylthymidine	7791-71-1	C₂₉H₂₈N₂O₅	484.552
保护胸苷	5'-O-(4-4'-dimethoxytrityl)thymidine	40615-39-2	C₃₁H₃₂N₂O₇	544.604
——	5'-O-(4-monomethoxytrityl)-2'-deoxythymidine	42926-80-7	C₃₀H₃₀N₂O₆	514.578
——	1-{5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione	1093730-81-4	C₃₁H₃₂N₂O₇	544.604

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	1-(3'-O-tert.-Butyldiphenylsilyl-2',5'-dideoxy-β-D-erythro-pentafuranosyl)-thymine	138840-77-4	C₂₆H₃₂N₂O₄Si	464.637
——	3'-O-tert-Butyldiphenylsilyl-5'-O-methanesulfonyl-thymidine	138840-74-1	C₂₇H₃₄N₂O₇SSi	558.728
——	1-(2-deoxy-3-O-tert-butyldiphenylsilyl-β-D-erythro-pentadialdo-1,4-furanosyl)-5-methyluracil	146604-43-5	C₂₆H₃₀N₂O₅Si	478.62
——	(2S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydrofuran-2-carboxylic acid	127244-82-0	C₂₆H₃₀N₂O₆Si	494.62
——	(E)-6'-bromo-(5'-deoxy-5'-methylidene)-3'-O-(tert-bytuldiphenylsilyl)thymidine	236754-84-0	C₂₇H₃₁BrN₂O₄Si	555.544
——	(Z)-6'-bromo-(5'-deoxy-5'-methylidene)-3'-O-(tert-butyldiphenylsilyl)thymidine	——	C₂₇H₃₁BrN₂O₄Si	555.544
——	6'-dibromo-(5'deoxy-5'-methylidene)-3'-O-(tert-butyldiphenylsilyl)thymidine	181999-83-7	C₂₇H₃₀Br₂N₂O₄Si	634.44
——	TBDPS(-3)2,6-deoxy-L-lyxHexf5N(a)-thymin-1-yl	199458-05-4	C₂₇H₃₅N₃O₄Si	493.678
——	TBDPS(-3)Digf5N(b)-thymin-1-yl	199458-20-3	C₂₇H₃₅N₃O₄Si	493.678
——	(2S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydrofuran-2-carboxylic acid tert-butyl ester	127218-27-3	C₃₀H₃₈N₂O₆Si	550.727
——	1-[(2R,4S,5R)-5-[[[(2R,3S,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-methylphosphanyl]oxymethyl]-4-[tert-butyl(diphenyl)silyl]oxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione	189384-00-7	C₄₃H₆₁N₄O₁₀PSi₂	881.123
——	3'-O-tert-butyldiphenylsilyl-5'-(R)-C-dimethylphosphonothymidine	264141-41-5	C₂₈H₃₇N₂O₈PSi	588.67
——	3'-O-tert-butyldiphenylsilyl-5'-(S)-C-dimethylphosphonothymidine	634206-60-3	C₂₈H₃₇N₂O₈PSi	588.67
——	3'-O-tert-butyldiphenylsilyl-5'-hydroxy-5'-C(S)-tosyloxyethyl-thymidine	494798-47-9	C₃₅H₄₂N₂O₈SSi	678.879
——	(S)-N-[(1S)-1-[(2R,3S,5R)-3-[tert-butyl(diphenyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]ethyl]-2-methylpropane-2-sulfinamide	521065-39-4	C₃₁H₄₃N₃O₅SSi	597.851
——	dimethyl 3'-O-tert-butyldiphenylsilyl-5'-O-isopropoxycarbonylthymidin-5'-C-ylphosphonate	——	C₃₂H₄₃N₂O₁₀PSi	674.76
——	Diphenyl-phosphinic acid (2R,3S,5R)-5-(4-amino-5-methyl-2-oxo-2H-pyrimidin-1-yl)-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-ylmethoxymethyl ester	173034-02-1	C₃₉H₄₄N₃O₆PSi	709.854
——	1-[(2R,4S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-[[(E)-2-[(2R,3S,5R)-3-[tert-butyl(diphenyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]ethenyl]-methoxyphosphoryl]oxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione	289711-56-4	C₄₄H₆₁N₄O₁₁PSi₂	909.133
——	[(2R,3S,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] [(2R,3S,5R)-3-[tert-butyl(diphenyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl [(2S)-1-cyano-3-(1H-indol-2-yl)propan-2-yl] phosphite	214150-14-8	C₅₄H₆₉N₆O₁₁PSi₂	1065.32
——	[(2S)-1-[tert-butyl(dimethyl)silyl]oxy-3-(1H-indol-2-yl)propan-2-yl] [(2R,3S,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] [(2R,3S,5R)-3-[tert-butyl(diphenyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl phosphite	1053693-68-7	C₅₉H₈₄N₅O₁₂PSi₃	1170.57
——	5'-O-(4,4'-dimethoxytrityl)thymidinyl 2-cyanoethylphosphono-[3'(O)->5'(C)]-5'-deoxy-5'-methylidene-3'-O-(tert-butyldiphenylsilyl)thymidine	——	C₆₁H₆₆N₅O₁₃PSi	1136.28
——	5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidinyl 2-cyanoethylphosphono-[3'(O)->5'(C)]-5'-deoxy-5'-methylidene-3'-O-(tert-butyldiphenylsilyl)thymidine	——	C₆₇H₆₉N₆O₁₃PSi	1225.38
——	5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosinyl methylphosphono [3'(O)->5'(C)]-5'-deoxy-5'-methylidene-3'-O-(tert-butyldiphenylsilyl)thymidine	——	C₆₈H₆₉N₈O₁₂PSi	1249.4
——	1-[(2R,4S,5S)-4-hydroxy-5-hydroxymethyl-5-(2-propenyl)tetrahydrofuran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione	339178-14-2	C₁₃H₁₈N₂O₅	282.296
——	(2S,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-carboxylic acid tert-butyl ester	339178-10-8	C₁₄H₂₀N₂O₆	312.323
——	(E)-6'-bromo-(5'-deoxy-5'-methylidene)thymidine	375352-47-9	C₁₁H₁₃BrN₂O₄	317.139
——	1-(2-deoxy-4-methoxy-β-D-ribofuranosyl)thymine	140226-29-5	C₁₁H₁₆N₂O₆	272.258
——	tert-butyl (2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-prop-2-enyloxolane-2-carboxylate	339178-18-6	C₁₇H₂₄N₂O₆	352.387
——	(6'-diethoxyphosphonate-3'-O-methanesulphonyl-2',5',6'-trideoxy-β-D-lyxo-hexofuranosyl)-1-thymine	124685-25-2	C₁₆H₂₇N₂O₉PS	454.438
——	1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-5-phenylselenenyltetrahydrofuran-2-yl)-5-methyl-1H-pyrimidine-2,4-dione	164864-68-0	C₁₆H₁₈N₂O₅Se	397.289
——	(2S,3S,5R)-3-benzenesulfonyloxy-2-fluoro-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-carboxylic acid tert-butyl ester	339178-22-2	C₂₀H₂₃FN₂O₈S	470.476
——	(2S,4S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(phenylselenenyl)tetrahydrofuran-2-carboxylic acid tert-butyl ester	339178-17-5	C₂₀H₂₄N₂O₆Se	467.38
——	(2R,4S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(phenylselenenyl)tetrahydrofuran-2-carboxylic acid tert-butyl ester	——	C₂₀H₂₄N₂O₆Se	467.38
——	5'-O-(4,4'-dimethoxytrityl)thymidinyl 2-cyanoethylphosphono-[3'(O)->5'(C)]-(5'-deoxy-5'-methylidene)thymidine	——	C₄₅H₄₈N₅O₁₃P	897.876
{2-[(2R,3S,5R)-3-叠氮-5-(5-甲基-2,4-二羰基-3,4-二氢嘧啶-1(2H)-基)四氢呋喃-2-基]乙基}膦酸	6'-<(3'-azido-2',3',5',6'-tetradeoxy-β-D-ribo-hexofuranosyl)-1-thymine>-phosphonic acid	124685-20-7	C₁₁H₁₆N₅O₆P	345.252
——	1-[(2R,4S,5S)-5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-(4-{(2R,3S,5R)-3-hydroxy-5-[5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]tetrahydrofuran-2-yl}-1H-1,2,3-triazol-1-yl)tetrahydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione	1262311-81-8	C₄₂H₄₃N₇O₁₀	805.844
——	5'-O-(4,4'-dimethoxytrityl)thymidinyl 2-cyanoethylphosphono-[3'(O)->5'(C)]-(5'-deoxy-5'-methylidene)thymidine-3'-O-(N,N-diisopropylamino-2-cyanoethyl) phosphoramidite	——	C₅₄H₆₅N₇O₁₄P₂	1098.1
——	(2R,3S,5R)-2-({1-[(2S,3S,5R)-2-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-5-[5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]tetrahydrofuran-3-yl]}-1H-1,2,3-triazol-4-yl)-5-[5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]tetrahydrofuran-3-yl 2-cyanoethyl diisopropylphosphoramidite	1262311-78-3	C₅₁H₆₀N₉O₁₁P	1006.06
1,4-脱水-2-脱氧-3-O-[(叔丁基)二苯基硅]-D-赤式-戊-1-烯糖醇	((2R,3S)-3-(tert-butyldiphenylsilyloxy)-2,3-dihydrofuran-2-yl)methanol	130277-32-6	C₂₁H₂₆O₃Si	354.521

反应信息

作为反应物：

描述：

1-[(2R,4S,5R)-4-(tert-butyldiphenylsilanyloxy)-5-hydroxymethyltetrahydrofuran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 在二甲基亚砜、 N,N'-二环己基碳二亚胺作用下，生成 1-(2-deoxy-3-O-tert-butyldiphenylsilyl-β-D-erythro-pentadialdo-1,4-furanosyl)-5-methyluracil

参考文献：

名称：

含有3'-烯丙基醚，3'-烯丙基硫醚及其饱和衍生物作为磷酸盐模拟物的寡脱氧核苷酸

摘要：

已经制备了一系列含有3'-烯丙基，3'-烯丙基硫键及其饱和衍生物的新型胸苷-胸苷二聚体，并将其掺入寡脱氧核苷酸（ODN）中。3'-烯丙基类似物仅导致相对于磷酸二酯键具有互补ssRNA的双螺旋形成的适度去稳定。这个事实及其容易的合成可能表明这种连接在基于寡核苷酸的治疗剂中的应用。

DOI：

10.1016/0040-4039(94)85210-3
作为产物：

描述：

beta-胸苷在咪唑、 N-溴代丁二酰亚胺(NBS) 、三氟乙酸、锌作用下，以溶剂黄146 为溶剂，反应 5.0h，生成 1-[(2R,4S,5R)-4-(tert-butyldiphenylsilanyloxy)-5-hydroxymethyltetrahydrofuran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

参考文献：

名称：

A Novel Route to Pyrimidine Nucleosides via Intramolecular Couplings of Bases with 2′-Deoxyribosides: Quick and Stereospecific...but with a 'Twist'

摘要：

将嘧啶基（例如，胸腺嘧啶）与2'-脱氧核糖的C-5'羟基通过溴醚化偶联，会产生中间体，可以在路易斯酸的作用下转化为环核苷。通过β-消除反应开环，得到在所需的异头位置上具有立体纯度的核苷。

DOI：

10.1055/s-1994-25717

点击查看最新优质反应信息

文献信息

Selective Cleavage of O-(Dimethoxytrityl) Protecting Group with Sodium Periodate

作者：Dominik Rejman、Šárka Králíková、Zdeněk Točík、Radek Liboska、Ivan Rosenberg

DOI：10.1135/cccc20020502

日期：——

Sodium periodate in aqueous organic solvents selectively removes, under mild reaction conditions, the O-(dimethoxytrityl) protecting group. Selectivity of the cleavage was studied using the nucleoside derivatives protected by various types of groups commonly used in nucleoside and nucleotide chemistry.

在水有机溶剂中，过碘酸钠在温和的反应条件下选择性地去除了O-(二甲氧基三苯甲基)保护基团。利用核苷衍生物进行了裂解的选择性研究，这些核苷衍生物受到核苷和核苷酸化学中常用的各种基团的保护。
Synthesis of Disaccharide Nucleosides by theO-Glycosylation of Natural Nucleosides with Thioglycoside Donors

作者：Shin Aoki、Taketo Fukumoto、Taiki Itoh、Masayuki Kurihara、Shigeto Saito、Shin-ya Komabiki

DOI：10.1002/asia.201403319

日期：2015.3

Disaccharide nucleosides constitute an important group of naturally‐occurring sugar derivatives. In this study, we report on the synthesis of disaccharide nucleosides by the direct O‐glycosylation of nucleoside acceptors, such as adenosine, guanosine, thymidine, and cytidine, with glycosyl donors. Among the glycosyl donors tested, thioglycosides were found to give the corresponding disaccharide nucleosides

二糖核苷是天然存在的糖衍生物的重要组成部分。在这项研究中，我们报道了通过核苷受体（如腺苷，鸟苷，胸苷和胞苷）与糖基供体的直接O-糖基化来合成二糖核苷。在测试的糖基供体中，发现硫代糖苷可以使用对甲苯磺酰氯（TolSCl）和三氟甲磺酸银（AgOTf）作为促进剂，以上述核苷受体以中等至高化学产率提供相应的二糖核苷。通过1 H NMR光谱实验检查了这些启动子与核苷受体的相互作用。
[EN] COMPOUNDS, COMPOSITIONS AND METHODS FOR SYNTHESIS [FR] COMPOSÉS, COMPOSITIONS ET PROCÉDÉS DE SYNTHÈSE

申请人：WAVE LIFE SCIENCES LTD

公开号：WO2018237194A1

公开（公告）日：2018-12-27

The present disclosure, among other things, provides technologies for synthesis, including reagents and methods for stereoselective synthesis. In some embodiments, the present disclosure provides compounds useful as chiral auxiliaries. In some embodiments, the present disclosure provides reagents and methods for oligonucleotide synthesis. In some embodiments, the present disclosure provides reagents and methods for chirally controlled preparation of oligonucleotides. In some embodiments, technologies of the present disclosure are particularly useful for constructing challenging internucleotidic linkages, providing high yields and stereoselectivity.

本公开内容提供了合成技术，包括用于立体选择性合成的试剂和方法。在某些实施例中，本公开内容提供了作为手性辅助剂有用的化合物。在某些实施例中，本公开内容提供了用于寡核苷酸合成的试剂和方法。在某些实施例中，本公开内容提供了用于手性控制寡核苷酸制备的试剂和方法。在某些实施例中，本公开内容的技术特别适用于构建具有挑战性的核苷酸间连接，提供高产率和立体选择性。
[EN] LINKAGE MODIFIED OLIGOMERIC COMPOUNDS [FR] COMPOSÉS OLIGOMÈRES MODIFIÉS PAR LIAISON

申请人：ISIS PHARMACEUTICALS INC

公开号：WO2015168172A1

公开（公告）日：2015-11-05

The present invention provides oligomeric compounds comprising at least one neutral methoxypropyl phosphonate modified internucleoside linkage. Such oligomeric compounds have one or more improved properties such as selectivity, potency, improved toxicity profile and or improved proinflammatory profile. Such oligomeric compounds have enhanced stability to exposure to base during synthesis. Certain such oligomeric compounds are useful for hybridizing to a complementary nucleic acid, including but not limited, to nucleic acids in a cell. In certain embodiments, hybridization results in modulation of the amount activity or expression of the target nucleic acid in a cell.

本发明提供了含有至少一种中性甲氧基丙基磷酸酯修饰的核苷间连接的寡聚化合物。这种寡聚化合物具有一个或多个改进的性质，如选择性、效力、改进的毒性谱和/或改进的促炎谱。这种寡聚化合物在合成过程中对碱的暴露具有增强的稳定性。某些这种寡聚化合物对于与细胞中的互补核酸杂交是有用的，包括但不限于核酸。在某些实施例中，杂交导致调节细胞中目标核酸的活性或表达量。
[EN] NOVEL PHOSPHOROUS (V)-BASED REAGENTS, PROCESSES FOR THE PREPARATION THEREOF, AND THEIR USE IN MAKING STEREO-DEFINED ORGANOPHOSHOROUS (V) COMPOUNDS [FR] NOUVEAUX RÉACTIFS À BASE DE PHOSPHORE (V), LEURS PROCÉDÉS DE PRÉPARATION ET LEUR UTILISATION DANS LA FABRICATION DE COMPOSÉS ORGANOPHOSHOREUX (V) STÉRÉODÉFINIS

申请人：BRISTOL MYERS SQUIBB CO

公开号：WO2019200273A1

公开（公告）日：2019-10-17

The present invention relates to novel phosphorous (V) (P(V)) reagents, methods for preparing thereof, and methods for preparing organophosphorous (V) compounds by using the novel reagents.

本发明涉及新型磷（V）（P(V)）试剂，其制备方法以及利用这种新型试剂制备有机磷（V）化合物的方法。