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2',3'-benzylideneadenosine | 3257-69-0

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',3'-benzylideneadenosine

英文别名

2',3'-O,O-benzylidene adenosine；2',3'-O-Benzylidenadenosin；2',3'-O-benzylideneadenosine；O^2'_,O3'-benzylidene-adenosine；[(3aR,4R,6R,6aR)-4-(6-aminopurin-9-yl)-2-phenyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methanol

CAS

3257-69-0

化学式

C₁₇H₁₇N₅O₄

mdl

——

分子量

355.353

InChiKey

SUQRZCNRGOUISV-NNYHISJYSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

660.6±65.0 °C(Predicted)
密度：

1.75±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

0.78
重原子数：

26.0
可旋转键数：

3.0
环数：

5.0
sp3杂化的碳原子比例：

0.35
拓扑面积：

117.54
氢给体数：

2.0
氢受体数：

9.0

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
腺苷	adenosine	58-61-7	C₁₀H₁₃N₅O₄	267.244

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	2',3'-O-benzylidene-5'-O-(tert-butyldimethylsilyl)adenosine	1356085-05-6	C₂₃H₃₁N₅O₄Si	469.616
——	2',3'-benzylidene-5'-adenosine	114958-16-6	C₂₄H₂₀FN₅O₇S	541.517
——	4-Sulfamoyl-benzoic acid (3aR,4R,6R,6aR)-6-(6-amino-purin-9-yl)-2-phenyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester	114958-17-7	C₂₄H₂₂N₆O₇S	538.541
——	6-N-benzyloxycarbonyl-2',3'-O-benzylideneadenosine	1356085-12-5	C₂₅H₂₃N₅O₆	489.488
——	4-Benzylsulfamoyl-benzoic acid (3aR,4R,6R,6aR)-6-(6-amino-purin-9-yl)-2-phenyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester	114958-22-4	C₃₁H₂₈N₆O₇S	628.665
——	4-(3-Phenyl-propylsulfamoyl)-benzoic acid (3aR,4R,6R,6aR)-6-(6-amino-purin-9-yl)-2-phenyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester	114958-28-0	C₃₃H₃₂N₆O₇S	656.719
——	4-Phenethylsulfamoyl-benzoic acid (3aR,4R,6R,6aR)-6-(6-amino-purin-9-yl)-2-phenyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester	114958-25-7	C₃₂H₃₀N₆O₇S	642.692
——	4-Phenylsulfamoyl-benzoic acid (3aR,4R,6R,6aR)-6-(6-amino-purin-9-yl)-2-phenyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester	114958-20-2	C₃₀H₂₆N₆O₇S	614.638
——	6-N-benzyloxycarbonyl-2',3'-O-benzylidene-5'-sulfamoyladenosine	1356085-15-8	C₂₅H₂₄N₆O₈S	568.567
——	6-N-benzyloxycarbonyl-2',3'-O-benzylidene-5'-O-(tert-butyldimethylsilyl)adenosine	1356085-09-0	C₃₁H₃₇N₅O₆Si	603.75
——	6-N-benzyloxycarbonyl-2',3'-O-benzylidene-5'-O-[N-(N-Cbz-L-lysinyl(ε-Cbz))sulfamoyl]adenosine	1356085-21-6	C₄₇H₄₈N₈O₁₃S	965.01
——	6-N-benzyloxycarbonyl-2',3'-O-benzylidene-5'-O-[N-(N-Cbz-L-valinyl)sulfamoyl]adenosine	1356085-18-1	C₃₈H₃₉N₇O₁₁S	801.834
——	6-N-benzyloxycarbonyl-2',3'-O-benzylidene-5'-O-[N-(N-Cbz-L-ornithinyl(δ-Cbz))-sulfamoyl]adenosine	1356085-27-2	C₄₆H₄₆N₈O₁₃S	950.983
——	6-N-benzyloxycarbonyl-2',3'-O-benzylidene-5'-O-[N-(2,4-di(benzyloxycarbonylamino)-L-butyryl)sulfamoyl]adenosine	1356085-24-9	C₄₅H₄₄N₈O₁₃S	936.956
——	6-N-benzyloxycarbonyl-2',3'-O-benzylidene-5'-O-[N-(N-Cbz)-L-homoserinyl(OBn)sulfamoyl]adenosine	1356085-30-7	C₄₄H₄₃N₇O₁₂S	893.931
——	4-Benzylsulfamoyl-benzoic acid (2R,3S,4R,5R)-5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester	114958-10-0	C₂₄H₂₄N₆O₇S	540.557
——	5'-<4-(phenoxysulfonyl)benzoyl>adenosine	114958-13-3	C₂₃H₂₁N₅O₈S	527.514
——	4-(3-Phenyl-propylsulfamoyl)-benzoic acid (2R,3S,4R,5R)-5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester	114958-12-2	C₂₆H₂₈N₆O₇S	568.61
——	4-Phenethylsulfamoyl-benzoic acid (2R,3S,4R,5R)-5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester	114958-11-1	C₂₅H₂₆N₆O₇S	554.583
——	5'-<4-(anilinosulfonyl)benzoyl>adenosine	114958-09-7	C₂₃H₂₂N₆O₇S	526.53
——	6-N-benzyloxycarbonyl-2',3'-O-benzylidene-5'-O-[N-(N-Cbz-L-tyrosyl(OBn))sulfamoyl]adenosine	1356085-35-2	C₄₉H₄₅N₇O₁₂S	956.002
——	6-N-benzyloxycarbonyl-2',3'-O-benzylidene-5'-O-[N-(N-Cbz)-L-serinyl(P(O)(OBn)2)sulfamoyl]adenosine	1356085-33-0	C₅₀H₄₈N₇O₁₅PS	1050.01
——	5′-O-[N-(valinyl)sulfamoyl]adenosine	312493-34-8	C₁₅H₂₃N₇O₇S	445.456
——	4-[4-(2-Acetylamino-2-carbamoyl-ethyl)-phenoxysulfonyl]-benzoic acid (2R,3S,4R,5R)-5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester	114958-14-4	C₂₈H₂₉N₇O₁₀S	655.645
——	5'-O-(tyrosylsulfamoyl)adenosine	——	C₁₉H₂₃N₇O₈S	509.5
——	6-N-benzyloxycarbonyl-2',3'-O-benzylidene-5'-O-[N-(N-Cbz-L-tryptophanyl)sulfamoyl]adenosine	1356085-37-4	C₄₄H₄₀N₈O₁₁S	888.915
——	5'-O-(N-tryptophanylsulfamoyl)adenosine	312493-40-6	C₂₁H₂₄N₈O₇S	532.537

反应信息

作为反应物：

描述：

2',3'-benzylideneadenosine 在 4-二甲氨基吡啶、 sodium hydride 、三氟乙酸作用下，以 N,N-二甲基甲酰胺为溶剂，反应 19.0h，生成 5'-<4-(phenoxysulfonyl)benzoyl>adenosine

参考文献：

名称：

癌基因编码酪氨酸特异性蛋白激酶的多底物抑制剂的合成和评估。1。

摘要：

描述了酪氨酸特异性蛋白激酶潜在的多底物抑制剂的合成和测试。底物之一，ATP，是由已知的激酶抑制剂5'-[4-（氟磺酰基）苯甲酰基]腺苷模拟的，后者通过磺酰基部分与酪氨酸模拟物共价连接。测试了所得的多底物抑制剂通过p60v-abl抑制磷酸从ATP转移到蛋白质受体的能力，p60v-abl是由Abelson鼠白血病病毒（A-MuLV）的转化基因（v-abl）编码的酪氨酸激酶。尽管一系列抑制剂显示出中等强度的活性（IC50值低至19 microM），酪氨酸模拟物的修饰没有产生大的影响，这表明它们不作为多底物抑制剂起作用，而是主要通过所有抑制剂共有的腺苷部分结合。通过发现抑制剂缺乏特异性，在相当的浓度下抑制丝氨酸激酶的发现，加强了这种解释。

DOI：

10.1021/jm00117a015
作为产物：

描述：

在三氟乙酸作用下，以二氯甲烷为溶剂，反应 1.5h，生成 2',3'-benzylideneadenosine

参考文献：

名称：

5'-O-[N-(酰基)氨磺酰基]腺苷衍生物的固相合成

摘要：

描述了 5'-O-[N-（酰基）氨磺酰基] 腺苷衍生物的固相合成。使用 Rink 酰胺聚苯乙烯固体载体和适当保护的核糖嘌呤起始材料，为 5'-O-[N-(酰基)氨磺酰基]的固相合成开发了一种高度可靠和实用的路线腺苷。开发的程序能够以高产率高效并行合成目标化合物。这些化合物是酰基腺苷酸的不可水解等排体，它们在一系列不同的代谢途径中发挥重要作用，例如核糖体和非核糖体肽合成、脂肪酸氧化或酶调节；一些形成腺苷酸的酶是潜在的药物靶点。

DOI：

10.1002/ejoc.201200329

点击查看最新优质反应信息

文献信息

Synthesis of adenosine-5′-phosphates and 5′-alkylphosphonates via the Mitsunobu reaction

作者：Mourad Saady、Luc Lebeau、Charles Mioskowski

DOI：10.1016/0040-4039(95)00234-4

日期：1995.3

The Mitsunobu reaction can be successfully applied to achieve phosphorylation and phosphonylation of purine nucleosides. A series of different adenosine-5′-phosphate analogs was obtained with good to excellent yields.

Mitsunobu反应可以成功地用于实现嘌呤核苷的磷酸化和膦酰化。获得了一系列不同的具有良好至优异产率的不同的腺苷-5'-磷酸类似物。
Investigation, optimization and synthesis of sulfamoyloxy-linked aminoacyl-AMP analogues

作者：Itedale Namro Redwan、Thomas Ljungdahl、Morten Grøtli

DOI：10.1016/j.tet.2011.12.011

日期：2012.2

Aminoacyl-tRNA synthetases (aaRSs) constitute a family of enzymes that transfer amino acids to their corresponding tRNA molecules to form aminoacyl-tRNAs and have been validated as potential drug targets. Sulfamoyloxy-linked aminoacyl-AMP analogues are potent inhibitors of aaRSs. In this article, we report the synthesis of several new sulfamoyl analogues of as-AMP that up to now have been difficult or even impossible to prepare with current synthetic strategies. The developed synthetic strategy relies on performing the synthesis under neutral conditions followed by global deprotection using catalytic hydrogenation affording the desired 5'-0-(N-aminoacyl)sulfamoyladenosine compounds. (C) 2011 Elsevier Ltd. All rights reserved.
Synthesis of Two Stable Nitrogen Analogues of <i>S</i>-Adenosyl-<scp>l</scp>-methionine

作者：Mark J. Thompson、Abdelaziz Mekhalfia、David P. Hornby、G. Michael Blackburn

DOI：10.1021/jo9907742

日期：1999.10.1

Homochiral syntheses of two stable nitrogen analogues of S-adenosyl-L-methionine (AdoMet) are described. In the first analogue, AzaAdoMet, the sulfonium center of AdoMet, is replaced by an N-methyl moiety whose pK(a) is 7.08. This provides a charge-switchable analogue of AdoMet whose ionic state is a function of the pH. A second analogue, MeAzaAdoMet, has a quaternary dimethylammonium group in place of the methylsulfonium center of AdoMet: thus, its ionic state is independent of pH.
Synthesis of 8-aminoadenosine 5′-(aminoalkyl phosphates), analogues of aminoacyl adenylates

作者：Esmail Yousefi-Salakdeh、Merita Murtola、Anders Zetterberg、Esther Yeheskiely、Roger Strömberg

DOI：10.1016/j.bmc.2005.11.049

日期：2006.4

A short and efficient route for the synthesis of aminoalkyl 8-aminoadenylates, potential aminoacyl-tRNA synthetase inhibitors, is presented. Aminoalkyl 8-aminoadenylates were synthesized using a 5'-H-phosphonate strategy involving minimal protecting group manipulations and a sing-le final deprotection step. (c) 2005 Elsevier Ltd. All rights reserved.
KRUSE, CAROLYN H.;HOLDEN, KENNETH G.;PRITCHARD, M. LYNN;FEILD, JOHN A.;RI+, J. MED. CHEM., 31,(1988) N 9, C. 1762-1767

作者：KRUSE, CAROLYN H.、HOLDEN, KENNETH G.、PRITCHARD, M. LYNN、FEILD, JOHN A.、RI+

DOI：——

日期：——