Reacción #417912

Ecuación de reacción

1,4-anhydro-2-O-benzyl-5-O-[bis(4-methoxyphenyl)(phenyl)methyl]D-ribitol

N,N-diisopropylethylamine

2-cyanoethyl-N,N-diisopropylchlorophosphoramidite

1-methylimidazole

→

pure product

Rendimiento 42.6%

1,4-Anhydro-2-O-benzyl-5-O-[bis(4-methoxyphenyl)(phenyl)methyl]-3-O-[(2-cyanoethoxy)(dipropan-2-ylamino)phosphanyl]-D-ribitol

Rendimiento 42.6%

Disolventes

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction was then quenched with methanol (5 mL)
2. 2
   workup.STIRRINGstirred for 5 min
3. 3
   OtroThe solvent was then removed in vacuo
4. 4
   Otrothe residue was purified by flash chromatography

Procedimiento

To a cooled solution (0° C.) of 1,4-anhydro-2-O-benzyl-5-O-[bis(4-methoxyphenyl)(phenyl)methyl]D-ribitol (1.60 g, 3.04 mmol) and N,N-diisopropylethylamine (1.59 mL, 9.11 mmol) in DCM (20 mL), 2-cyanoethyl-N,N-diisopropylchlorophosphoramidite (1.44 g, 6.08 mmol) and 1-methylimidazole (0.12 mL, 1.519 mmol) were added. The reaction mixture was warmed to ambient temperature and stirred for 90 min. The reaction was then quenched with methanol (5 mL) and stirred for 5 min. The solvent was then removed in vacuo, and the residue was purified by flash chromatography using 20% ethyl acetate in hexane to obtain 0.94 g (1.293 mmol, 42.6%) of the pure product. LCMS: for C42H51N2O7P calculated 726.3. found 727.3 [M+H]+ and 749.4 [M+Na]+. 31P NMR (400 MHz, CD3CN) δ: 149.94, 149.70.

Fuente