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HRID1871211

反应详情

EQUATION

反应方程式

HRID 1871211 的结构方程式

REACTANTS

反应物

3
结构：C(=NC1CCCCC1)=NC1CCCCC1
HCID10868

Dicyclohexylcarbodiimide

C13H22N2

结构：CCCCCCCCCCCCCCCC(=O)OC[C@H]1O[C@@H](n2ccc(N)nc2=O)C[C@@H]1O
HCID15484389

未命名化合物

结构：CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)[C@@H](CCCCN)C(=O)O
HCID22792075

未命名化合物

PRODUCTS

生成物

1
结构：CCCCCCCCCCCCCCCC(=O)OC[C@H]1O[C@@H](n2ccc(NC(=O)[C@@H](N)CCCCN)nc2=O)C[C@@H]1O
HCID15484390

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

1
结构：CC(=O)N(C)C
溶剂HCID31374

Dimethylacetamide

C4H9NO

CONDITIONS

反应条件

温度
4 °C

PROCEDURE

实验过程

14 grams of 5'-O-palmitoyl-deoxycytidine is dissolved in 100 ml dimethylacetamide, 1 molar equivalent of di-tert-butoxycarbonyl-lysine is added, and the mixture is cooled in an ice bath. 1.2 molar equivalents (7.4 g) of dicyclohexylcarbodiimide are added and the mixture is stirred at 4° C. for 90 hours. The precipitate (dicyclohexylurea) is removed by filtration. 100 ml of water is added to the filtrate, followed by 1 liter of ethyl acetate. N4 -(di-N-tert-butoxycarbonyl-lysyl)-5'-O-palmitoyl-deoxycyt-idine is separated from unreacted reagents by chromatography over silica gel. The t-butoxycarbonyl protecting groups are removed by the standard methods of treatment with an acid, such as trifluoroacetic acid.

WORKUP

后处理

  1. temperaturethe mixture is cooled in an ice bath
  2. customThe precipitate (dicyclohexylurea) is removed by filtration
  3. addition100 ml of water is added to the filtrate
  4. customN4 -(di-N-tert-butoxycarbonyl-lysyl)-5'-O-palmitoyl-deoxycyt-idine is separated from unreacted reagents by chromatography over silica gel
  5. customThe t-butoxycarbonyl protecting groups are removed by the standard methods of treatment with an acid, such as trifluoroacetic acid