反应 #59246

反应方程式

product

methyl-2,3,5-tris-O-(2,4-dichlorobenzyl)-1-O-methyl-D-ribofuranose

SnCl4

→

methyl-3,5-bis-O-(2,4-dichlorobenzyl)-1-O-methyl-D-ribofuranose

溶剂

CH2Cl2

CH2Cl2

反应条件

后处理

1. 1
   workup.WAITthe solution was kept at 3° C. overnight
2. 2
   其他After 43 hours the reaction was quenched
3. 3
   workup.ADDITIONby carefully adding the solution to 1.9 L saturated NaHCO3 solution
4. 4
   其他Tin salts were removed via filtration through celite after which the organic phace
5. 5
   其他was isolated
6. 6
   干燥dried with MgSO4
7. 7
   其他evaporated in vacuo
8. 8
   其他The crude oil was used directly in the next step without further purification

实验过程

To a solution of the product of Step 1 (171.60 g, 0.2676 mol) in 1.8 L CH2Cl2 that was cooled to 0° C., was added dropwise a solution of stannous chloride (31.522 mL, 0.2676 mol) in 134 mL CH2Cl2 while stirring. After the solution was kept at 3° C. for 27 hours, another 5.031 ml of SnCl4 (0.04282 mol) was added and the solution was kept at 3° C. overnight. After 43 hours the reaction was quenched by carefully adding the solution to 1.9 L saturated NaHCO3 solution. Tin salts were removed via filtration through celite after which the organic phace was isolated, dried with MgSO4 and evaporated in vacuo. The yield of raw, dark yellow oil was 173.6 g, which contains 2,4-dibenzoyl chloride. The crude oil was used directly in the next step without further purification.

来源