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HRID967346

反应详情

EQUATION

反应方程式

HRID 967346 的结构方程式

REACTANTS

反应物

2
结构：N#CC1=C(C#N)C(=O)C(Cl)=C(Cl)C1=O
HCID6775

2,3-Dichloro-5,6-dicyano-p-benzoquinone

C8Cl2N2O2

结构：COc1ccc(CO[C@@H]2[C@@H](N=[N+]=[N-])[C@H](SC)O[C@H](CO[Si](c3ccccc3)(c3ccccc3)C(C)(C)C)[C@H]2OC(=O)c2ccccc2-c2ccccc2)cc1
HCID23396150

未命名化合物

PRODUCTS

生成物

1
结构：CS[C@@H]1O[C@H](CO[Si](c2ccccc2)(c2ccccc2)C(C)(C)C)[C@@H](OC(=O)c2ccccc2-c2ccccc2)[C@H](O)[C@H]1N=[N+]=[N-]
HCID23396149

未命名化合物

收率 93.4%

AUXILIARIES

试剂、催化剂与溶剂

1
结构：ClCCl.O
溶剂HCID21908982

未命名化合物

PROCEDURE

实验过程

A mixture of methyl 2-azido-4-O-biphenylcarbonyl-6-O-tert-butyldiphenylsilyl-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-62-D-glucopyranoside (11) (150 mg, 0.19 mmol) and DDQ (52 mg, 0.23 mmol) in CH2Cl2—H2O 9:1 (5 mL) was stirred at room temperature for 3 hours. The reaction mixture was washed with saturated NaHCO3 solution (3×3 ml), dried over MgSO4 and evaporated. The residue was purified by chromatography using EtOAc—hexane 15:85 as the mobile phase to give methyl 2-azido-4-O-biphenylcarbonyl-6-O-tert-butyldiphenylsilyl-2-deoxy-1-thio-β-D-glucopyranoside (41) (116 mg, 92%).

WORKUP

后处理

  1. washThe reaction mixture was washed with saturated NaHCO3 solution (3×3 ml)
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customThe residue was purified by chromatography