반응 #417912

반응 방정식

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

수율 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

수율 42.6%

용매

DCM

반응 조건

후처리

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

실험 절차

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.

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