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HRID1724638

反应详情

EQUATION

反应方程式

HRID 1724638 的结构方程式

REACTANTS

反应物

2
结构：CCC[CH2][Sn]([C]#N)([CH2]CCC)[CH2]CCC
HCID200512

Stannanecarbonitrile, tributyl-

C13H27NSn

结构：CC(=O)OC[C@H]1O[C@@H](n2cnc3c(NC4CCCC4)nc(I)nc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O
HCID14886862

未命名化合物

PRODUCTS

生成物

1
结构：CC(=O)OC[C@H]1O[C@@H](n2cnc3c(NC4CCCC4)nc(C#N)nc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O
HCID58767046

未命名化合物

收率 87.3%

AUXILIARIES

试剂、催化剂与溶剂

2
结构：c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1
催化剂HCID178418397

未命名化合物

结构：CN(C)C=O
溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

CONDITIONS

反应条件

温度
120 °C

PROCEDURE

实验过程

To a solution of (2R,3R,4R,5R)-4-acetyloxy-2-(acetyloxymethyl)-5-[6-(cyclopentylamino)-2-iodopurin-9-yl]oxolan-3-yl acetate (0.9 g, 1.53 mmol) in N,N-dimethylformamide (40 ml) was added tributyltin cyanide (0.58 g, 1.84 mmol) and tetrakis(triphenylphosphine)palladium (0.27 g, 0.23 mmol), and the mixture was stirred at 120° C. f overnight. Solvent was removed under reduced pressure, and the residue was dissolved in ethyl acetate and filtered through celite. The solvent was removed under reduced pressure, and the residue was chromatographed on silica gel, eluting with a mixture of ethanol/hexane 1:1, to provide (2R,3R,4R,5R)-4-acetyloxy-2-(acetyloxy-methyl)-5-[2-cyano-6-(cyclopentylamino)purin-9-yl]oxolan-3-yl acetate (0.65 g).

WORKUP

后处理

  1. customSolvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. filtrationfiltered through celite
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was chromatographed on silica gel
  6. washeluting with a mixture of ethanol/hexane 1:1