반응 #429103

반응 방정식

NH4OH

2'-O-methylguanosine

trimethylsilyl chloride

isobutyryl chloride

→

solid

N2-Isobutyryl-2'-O-methylguanosine

용매

H2O

pyridine

반응 조건

후처리

1. 1
   온도The reaction mixture was cooled in an ice bath
2. 2
   workup.STIRRINGafter stirring for 30 min the reaction mixture
3. 3
   기타was evaporated
4. 4
   기타The residue was triturated with H2O
5. 5
   여과filtered
6. 6
   기타the filtrate evaporated
7. 7
   기타purified by silica gel chromatography as per the procedure of Example 4

실험 절차

2'-O-methylguanosine (3.5 g) in pyridine (100 ml) was treated with trimethylsilyl chloride (9 ml, 6 eq) and isobutyryl chloride (6.2 ml) at RT for 4 hr. The reaction mixture was cooled in an ice bath, H2O (20 ml) was added and stirring continued for an additional 20 min. NH4OH (20 ml) was added and after stirring for 30 min the reaction mixture was evaporated. The residue was triturated with H2O, filtered and the filtrate evaporated and purified by silica gel chromatography as per the procedure of Example 4 to yield the product as an off white solid (1.5 g). 1H NMR (DMSO-d6) δ1.1 [d, 6, CH(CH3)2 ], 2.77 [m, 1, CH(CH3)2 ], 3.33-3.6 (m, 5, OCH3, H-5'), 3.93 (m, 1, H-4'), 4.22 (m, 1), 4.3 (m, 1), 5.1 (t, 1, 5'-OH), 5.28 (d, 1, 3'-OH), 5.9 (d, 1, H-1'), 8.28 (s, 1, H-8) and 11.9 (br s, 1, NH).

출처