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HRID967344

反应详情

EQUATION

反应方程式

HRID 967344 的结构方程式

REACTANTS

反应物

2
结构：[Na]
HCID5360545

Sodium

Na

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：COc1ccc(CO[C@H]2[C@H](O)[C@@H](CO[Si](c3ccccc3)(c3ccccc3)C(C)(C)C)O[C@@H](SC)[C@@H]2N=[N+]=[N-])cc1
HCID12114344

未命名化合物

收率 91.1%

AUXILIARIES

试剂、催化剂与溶剂

2
结构：CO
溶剂HCID887

Methanol

CH4O

结构：C1CCOC1
溶剂HCID8028

Tetrahydrofuran

C4H8O

CONDITIONS

反应条件

温度
40 °C

PROCEDURE

实验过程

Sodium (89 mg) was reacted in dry MeOH (50 mL) then a solution of methyl 2-azido-4-O-biphenylcarbonyl-6-O-tert-butyldiphenylsilyl-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D glucopyranoside (11) (3 g, 3.88 mmol) in THF (25 mL) was added. The reaction mixture was stirred at 40° C. for 30 minutes, then cooled to room temperature. The solution was neutralized by Amberlite IR 120 (H+) ion exchange resin. The suspension was filtered, the filtrate was evaporated. The residue was purified by chromatography using EtOAc—hexane 1:4 as the mobile phase to give methyl 2-azido-6-O-tert-butyldiphenylsilyl-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D glucopyranoside (10) (2.1 g, 91%).

WORKUP

后处理

  1. temperaturecooled to room temperature
  2. filtrationThe suspension was filtered
  3. customthe filtrate was evaporated
  4. customThe residue was purified by chromatography