Reacción #811982

Ecuación de reacción

2-iodoadenosine

diazomethane

tin chloride dihydrate methanol

→

Compound 47

2-iodo-2'-O-methyladenosine

Compound 48

2-iodo-3'-O-methyladenosine

Disolventes

1,2-dimethoxyethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGAfter stirring for one hour at room temperature
2. 2
   Concentraciónthe reaction mixture was concentrated to dryness under reduced pressure
3. 3
   Lavadoeluted with 40% (V/V) methanol in 0.1% (V/V) aqueous solution of TFA
4. 4
   LavadoFirst, 2-iodo-2'-O-methyladenosine (Compound 47) was eluted
5. 5
   Lavado2-iodo-3'-O-methyladenosine (Compound 48) was eluted
6. 6
   ConcentraciónBoth fractions were concentrated to dryness

Procedimiento

1.2 g of 2-iodoadenosine was suspended in 150 ml of 1 mmol tin chloride dihydrate/methanol. 50 ml of 0.4-0.5M diazomethane in 1,2-dimethoxyethane was added with stirring. After stirring for one hour at room temperature, the reaction mixture was concentrated to dryness under reduced pressure. The resulting product was applied on ODS column and eluted with 40% (V/V) methanol in 0.1% (V/V) aqueous solution of TFA. First, 2-iodo-2'-O-methyladenosine (Compound 47) was eluted, and then 2-iodo-3'-O-methyladenosine (Compound 48) was eluted. Both fractions were concentrated to dryness to give 135 mg of Compound 47 and 56 mg of Compound 48.

Fuente