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2'-脱氧尿嘧啶核苷 | 951-78-0

2'-脱氧尿嘧啶核苷
2'-Deoxyuridine
951-78-0
C9H12N2O5
228.201982498169
如需查看该化合物的详细结构式,mol文件,smile,InChi 请点击:2'-脱氧尿嘧啶核苷结构式
87566808
名称和标识符
MDL MFCD00006527
InChIKey MXHRCPNRJAMMIM-SHYZEUOFSA-N
Inchi 1S/C9H12N2O5/c12-4-6-5(13)3-8(16-6)11-2-1-7(14)10-9(11)15/h1-2,5-6,8,12-13H,3-4H2,(H,10,14,15)/t5-,6+,8+/m0/s1
SMILES O=C1NC(=O)C=CN1[C@H]1C[C@H](O)[C@@H](CO)O1
BRN 0024433
别名信息
- 中文别名 -
  • 2'-脱氧尿嘧啶核苷
  • 2'-脱氧尿苷
  • 2’-脱氧尿苷
  • 2ˊ-脱氧尿苷
  • 2‘-脱氧尿苷
  • 2′-脱氧尿苷
  • 2'-Deoxyuridine 2'-脱氧尿苷
  • 2-脱氧尿苷
  • 2'-脱氧尿苷,2'-Deoxyuridine
  • 5-硝基水杨醛
  • 2’-脱氧尿嘧啶核苷
  • 2'-去氧尿苷
  • 2'-脱氧尿甙
  • 2'-脱氧尿甙, 2'-脱氧尿嘧啶核苷
  • 去氧尿嘧啶核苷
  • 2′-dU 脱氧尿嘧啶核苷
- 英文别名 -
  • 1-((2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
  • 2-Deoxyuridine
  • Deoxyuridine
  • 2'-Deoxyuridine
  • 1-((2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydro-furan-2-yl)pyrimidine-2,4(1H,3H)-dione
  • 2`-Deoxyuridine
  • 2’-Deoxyuridine
  • 2'-Deoxyuridine-1’-d
  • [131I]-Deoxyuridine
  • [3H]-Deoxyuridine
  • 1-(2-Deoxy-β-D-ribofuranosyl)uracil
  • 2'-DEOXYTHYMIDINE-5'-DIPHOSPHATE TRISODIUM SALT
  • 2'-deoxy-uridin
  • 2'-dU
  • Deoxy-uridin
  • DEOXYURIDINE-2'
  • durd
  • Uracildeoxyr
  • Uracil deoxyriboside
  • 1-(2-Deoxy-b-D-erythro-pentofuranosyl)uracil
  • 2,4(1H,3H)-Pyrimidinedione, 1-(2-deoxy-b-D-erythro-pentofuranosyl)-
  • 2,4(1H,3H)-Pyrimidinedione,1-(2-deoxy-b-D-ribofuranosyl)-
  • 2'-Desoxyuridine
  • Deoxyribose uracil
  • NSC 23615
  • Uracildeoxyriboside
  • 2′-dU
  • Uridine, 2'-deoxy-
  • 1-(2-Deoxy-beta-D-ribofuranosyl)uracil
  • W78I7AY22C
  • 2 -Deoxyuridine
  • 1-(2-Deoxy-beta-D-erythro-pentofuranoxyl)uracil
  • 2,4(1H,3H)-Pyrimidinedione, 1-(2-deoxy-beta-D-ribofuranosyl)-
  • 2,4(1H,3H
  • 2′-Deoxyuridine (ACI)
  • 1-(2-Deoxy-β-D-erythro-pentofuranosyl)uracil
  • D
  • 2,4(1H,3H)-Pyrimidinedione, 1-(2-deoxy-β-D-erythro-pentofuranosyl)-
  • 2,4(1H,3H)-Pyrimidinedione, 1-(2-deoxy-β-D-ribofuranosyl)-
  • 2′-Desoxyuridine
  • MeSH ID: D003857
  • SR-01000091549
  • 2 inverted exclamation mark -Deoxyuridine
  • MXHRCPNRJAMMIM-UHFFFAOYSA-N
  • [5',5''-2H2]2'-DEOXYURIDINE
  • 1-(2-Deoxypentofuranosyl)pyrimidine-2,4(1H,3H)-dione
  • 2,4(1H,3H)-Pyrimidinedione, 1-(2-deoxy-.beta.-D-erythro-pentofuranosyl)-
  • FT-0665865
  • 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
  • AKOS026750183
  • 2'-DEOXYURIDINE-2-13C,1,3-15N2
  • URIDINE, 2-DEOXY-
  • NSC-23615
  • 2,3H)-Pyrimidinedione, 1-(2-deoxy-.beta.-D-erythro-pentofuranosyl)-
  • dURD
  • Desoxyuridine
  • Uracil desoxyuridine
  • SY038939
  • EU-0050286
  • SR-01000091549-1
  • [1',2',3',4',5'-13C5]2'-DEOXYURIDINE
  • 1-(2-Deoxy-.beta.-D-erythro-pentofuranoxyl)uracil
  • DTXSID60862484
  • AKOS005596404
  • LS-13642
  • [3'-13C]2'-DEOXYURIDINE
  • 369656-76-8
  • [2'-13C]2'-DEOXYURIDINE
  • FT-0612154
  • 2,4(1H,3H)-Pyrimidinedione, 1-(2-deoxy-.beta.-D-ribofuranosyl)-
  • NSC23615
  • 2,3H)-Pyrimidinedione, 1-(2-deoxy-.beta.-D-ribofuranosyl)-
  • SCHEMBL2641582
  • [1'-13C]2'-DEOXYURIDINE
  • MLS001066344
  • 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
  • Q419140
  • 1-(2-deoxy-beta-D-ribofuranosyl)-2,4(1H,3H)-Pyrimidinedione
  • DEOXYURIDINE [MI]
  • SCHEMBL28844
  • 1-(2-deoxy-beta-D-erythro-pentofuranosyl)uracil
  • O10766
  • 951-78-0
  • 1-[(4S,2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3-dihydropyrimidine-2, 4-dione
  • MFCD00006527
  • MXHRCPNRJAMMIM-SHYZEUOFSA-N
  • 1-(2-deoxy-beta-D-erythro-pentofuranosyl)-2,4(1H,3H)-Pyrimidinedione
  • 1-(2-deoxy-beta-delta-erythro-pentofuranosyl)-2,4(1H,3H)-Pyrimidinedione
  • BP-58660
  • 1-(2-Deoxy-delta-erythro-pentofuranosyl)uracil
  • 1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1-H-pyrimidine-2,4-dione
  • C00526
  • CCRIS 2832
  • Uridinie, 2'-deoxy-
  • 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione
  • AMY6955
  • ZINC00155696
  • 2'-DEOXYURIDINE
  • CHEBI:16450
  • D0060
  • E73B1553-A13A-4989-B045-A589A8F2B9DC
  • CS-W019820
  • BRN 0024433
  • 1-(2-DEOXY-.BETA.-D-ERYTHRO-PENTOFURANOSYL)URACIL
  • 2'-Deoxyuridine, >=98.5%
  • UNII-W78I7AY22C
  • 2,4(1H,3H)-Pyrimidinedione, 1-(2-deoxy-beta-D-erythro-ribofuranosyl)-
  • bmse000320
  • SMR000112296
  • CHEMBL353955
  • HY-D0186
  • 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
  • EINECS 213-455-7
  • AKOS015833069
  • 2'-Deoxyuridine-1'-d
  • PS-7750
  • s5505
  • DTXSID30883621
  • deoxyuridine
  • NCGC00142492-01
  • NS00014663
  • 1-(2-Deoxy-ss-D-ribofuranosyl)uracil
  • AKOS015896792
  • DB02256
  • HMS2267D16
  • 1-(2-Deoxy-D-erythro-pentofuranosyl)uracil
  • J-700048
  • EN300-7374520
  • DUR
  • 1-(2-deoxy-beta-delta-ribofuranosyl)-2,4(1H,3H)-Pyrimidinedione
  • CCG-247504
  • 2 inverted exclamation marka-dU
  • 2yb0
  • 2'-deoxyuridine
  • 2'-Deoxy-L-uridine
  • dU
  • MLSMR
物化性质
实验特性
LogP -1.82270
PSA 104.55000
Merck 2910
折射率 52 ° (C=1, 1mol/L NaOH)
水溶性 300 g/L (20 ºC)
沸点 370.01°C (rough estimate)
熔点 164.0 to 168.0 deg-C
闪点 No data available
颜色与性状 白色或类白色粉末状固体
溶解性 水溶性300 g/L (20°C)
敏感性 Air Sensitive
比旋光度 D22 +50° (c = 1.1 in N NaOH)
密度 1.3705 (rough estimate)
计算特性
精确分子量 228.07500
氢键供体数量 3
氢键受体数量 5
可旋转化学键数量 2
同位素质量 228.075
重原子数量 16
复杂度 343
同位素原子数量 0
确定原子立构中心数量 3
不确定原子立构中心数量 0
确定化学键立构中心数量 0
不确定化学键立构中心数量 0
共价键单元数量 1
疏水参数计算参考值(XlogP) -1.6
互变异构体数量 3
表面电荷 0
拓扑分子极性表面积 99.1
国际标准相关数据
EINECS 2832
海关数据
海关编码 29349990
生产方法和用途
用途 是生产抗肿瘤药FUDR、抗病毒药IDUR与BrDUR的原料药,并用作生化试剂
合成路线

合成路线:1 步

反应条件:
参考文献:
Removal of Acetal, Silyl, and 4,4'-Dimethoxytrityl Protecting Groups from Hydroxyl Functions of Carbohydrates and Nucleosides with Clay in Aqueous Methanol
Asakura, Jun-ichi; Robins, Morris J.; Asaka, Yukihiro; Kim, Tong Hei, Journal of Organic Chemistry, 1996, 61(25), 9026-9027

合成路线:1 步

反应条件:
参考文献:
A facile method for deprotection of trityl ethers using column chromatography
Pathak, Ashish K.; Pathak, Vibha; Seitz, Lainne E.; Tiwari, Kamal N.; Akhtar, Mohammad S.; et al, Tetrahedron Letters, 2001, 42(44), 7755-7757

合成路线:1 步

反应条件:
参考文献:
Use of Nucleoside Phosphorylases for the Preparation of Purine and Pyrimidine 2'-Deoxynucleosides
Drenichev, Mikhail S.; Alexeev, Cyril S.; Kurochkin, Nikolay N.; Mikhailov, Sergey N., Advanced Synthesis & Catalysis, 2018, 360(2), 305-312

合成路线:1 步

反应条件:
参考文献:
Preparation of 2'-deoxyuridine
, Japan, , ,

合成路线:1 步

反应条件:
参考文献:
Deoxynucleosides and related compounds. VII. Synthesis of 2'-deoxyuridine and of thymidine
Brown, D. M.; Parihar, D. B.; Reese, C. B.; Todd, Alexander, Journal of the Chemical Society, 1958, 3035, 3035-8

合成路线:1 步

反应条件:
参考文献:
Reactions of uracil and cytosine derivatives with sodium bisulfite. Specific deamination method
Shapiro, Robert; Servis, Robert E.; Welcher, Marvin, Journal of the American Chemical Society, 1970, 92, 422-4

合成路线:1 步

反应条件:
参考文献:
Improvement on the synthesis of 2'-deoxyuridine
Liang, Jian-feng; Song, Qi; Ye, Feng; Yang, Ji-mei; Zha, Qing; et al, Anhui Huagong, 2013, 39(6), 28-29

合成路线:1 步

反应条件:
参考文献:
Method for synthesizing 2'-deoxy-5-iodouridine from uracil
, China, , ,
相关文献
专业数据库参考
PubChemId 87566808
参考资料
Reaxys RN 24433
Beilstein 24433
化合物详情(旧版)

SMILES

OC[C@H]1O[C@H](C[C@@H]1O)N2C(=O)NC(=O)C=C2

产品用途
是生产抗肿瘤药FUDR、抗病毒药IDUR与BrDUR的原料药,并用作生化试剂
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