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HRID366972

反应详情

EQUATION

反应方程式

HRID 366972 的结构方程式

REACTANTS

反应物

3
结构：Nc1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)n1
HCID13711

2′-Deoxycytidine

C9H13N3O4

结构：BrBr
HCID24408

Bromine

Br2

结构：Nc1nc(=O)n([C@H]2C[C@H](OP(=O)(O)O)[C@@H](COP(=O)(O)O)O2)cc1O
HCID131719392

未命名化合物

PRODUCTS

生成物

1
结构：Nc1nc(=O)n([C@H]2C[C@H](O)[C@@H](CO)O2)cc1O
HCID477413

1-(2-Deoxypentofuranosyl)-4-imino-1,4-dihydropyrimidine-2,5-diol

C9H13N3O5

AUXILIARIES

试剂、催化剂与溶剂

1
结构：O
溶剂HCID962

Water

H2O

PROCEDURE

实验过程

5-Hydroxydeoxycytidine is synthesized in a similar manner to the published procedure of Eaton et al. (Biochem. Biophys. Acta 319:281-287, 1973) for 5-hydroxydeoxycytidine-3',5'-diphosphate. Bromine is added to a cooled (0° C.) solution of 2'-deoxycytidine (available from Sigma Chemical Company) in water until the yellow color persists. The excess bromine is quenched with cyclohexene and 2,4,6-collidine is added. After 2 hours, the reaction mixture is washed with ether and evaporated to dryness under vacuum. The crude 5-hydroxydeoxycytidine is then purified by reversed-phase HPLC on an ULTRASPHERE C18 column (Phenomenex) using a linear gradient of 0%-20% B in A (solvent A: 0.1 M NH4OAc, solvent B: 50% CH3CN in 0.1 M NH4OAc).

WORKUP

后处理

  1. customThe excess bromine is quenched with cyclohexene and 2,4,6-collidine
  2. additionis added
  3. washthe reaction mixture is washed with ether
  4. customevaporated to dryness under vacuum
  5. customThe crude 5-hydroxydeoxycytidine is then purified by reversed-phase HPLC on an ULTRASPHERE C18 column (Phenomenex)