Reaktion #1447116

Reaktionsgleichung

2′-C-methylcytidine

tert-butylmagnesium chloride

(9Z)-octadec-9-en-1-yl N-[chloro(4-chlorophenoxy)phosphoryl]-L-alaninate

→

title compound

5′-O-[(4-chlorophenoxy)[[(1S)-1-methyl-2-[(9Z)-9-octadecenyloxy]-2-oxoethyl]amino]phosphinyl]-2′-C-methylcytidine

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe crude mixture was purified by column chromatography on silica gel (DCM:MeOH gradient from 90:10 to 80:20)
2. 2
   workup.DISSOLUTIONthe resulting solid was redissolved in DMSO
3. 3
   Sonstigepurified by RP-HPLC

Vorschrift

Following the procedure described for Example 1, step 3, 2′-C-methylcytidine in THF (0.097 M) was cooled to −78° C., then tert-butylmagnesium chloride (as 1.0 M solution in THF, 2.2 eq.) was added followed by the addition of (9Z)-octadec-9-en-1-yl N-[chloro(4-chlorophenoxy)phosphoryl]-L-alaninate. The crude mixture was purified by column chromatography on silica gel (DCM:MeOH gradient from 90:10 to 80:20), the resulting solid was redissolved in DMSO and purified by RP-HPLC to afford the title compound as white powders. A 1:1.4* mixture of diastereoisomers at phosphorus was observed by 1H NMR.

Quelle