تفاعل #2200602

معادلة التفاعل

product

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

SnCl4

→

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

المذيبات

CH2Cl2

CH2Cl2

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر