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HRID1031431

反应详情

EQUATION

反应方程式

HRID 1031431 的结构方程式

REACTANTS

反应物

7
结构：Br
HCID260

Hydrogen Bromide

BrH

结构：O=c1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]1
HCID6029

Uridine

C9H12N2O6

结构：CC(=O)Br
HCID10482

Acetyl bromide

C2H3BrO

结构：CS(=O)(=O)Cl
HCID31297

Methanesulfonyl chloride

CH3ClO2S

结构：O=C([O-])c1ccccc1.[Na+]
HCID517055

Sodium benzoate

C7H5NaO2

结构：CS(=O)(=O)OC[C@H]1O[C@@H](n2ccc(=O)[nH]c2=O)[C@H](OS(C)(=O)=O)[C@@H]1OS(C)(=O)=O
HCID14133010

未命名化合物

结构：CS(=O)(=O)O[C@H]1[C@@H](Br)[C@H](n2ccc(=O)[nH]c2=O)O[C@@H]1COC(=O)c1ccccc1
HCID18640902

未命名化合物

PRODUCTS

生成物

1
结构：O=C(OC[C@@H]1CC[C@H](n2ccc(=O)[nH]c2=O)O1)c1ccccc1
HCID14308783

[(2S,5R)-5-(2,4-Dioxo-3,4-dihydropyrimidin-1(2H)-yl)oxolan-2-yl]methyl benzoate

C16H16N2O5

收率 60%

AUXILIARIES

试剂、催化剂与溶剂

6
结构：[Ni]
催化剂HCID935

Nickel

Ni

结构：[C].[Pd]
催化剂HCID178418390

未命名化合物

结构：CC(N)=O
溶剂HCID178

Acetamide

C2H5NO

结构：CCO
溶剂HCID702

Ethanol

C2H6O

结构：c1ccncc1
溶剂HCID1049

Pyridine

C5H5N

结构：CN(C)C=O
溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

Moreover, 2',3'-dideoxy-uridine or the derivatives thereof being the raw materials can be obtained easily from uridine being a constituting ingredient of ribonucleic acid by known method. For example, in the method described in Chem. Pharm. Bull., 18(3), 554-560, 1970, uridine is treated with methanesulfonyl chloride in pyridine solvent to convert to 2',3',5'-tri-O-methanesulfonyluridine and, by allowing this to react with sodium benzoate in acetamide or dimethylformamide solvent, 2,2'-anhydro-1-(5'-O-benzoyl-3'-O-mesyl-β-arabinosyl)uracil is obtained. This is allowed to react with hydrogen bromide or acetyl bromide to convert to 5'-O-benzoyl-2'-bromo-2'-deoxy-3'-O-mesyluridine and then this is treated with palladium carbon or Raney nickel catalyst in ethanol under atmosphere of hydrogen to obtain 5'-O-benzoyl-2',3'-dideoxy-uridine in a yield of about 60% (Chem. Pharm. Bull., 18(3), 554-560, 1970).

WORKUP

后处理

  1. customis obtained