2'-C-Methylcytidine → HCID 66973563, compound
Reaction equation
[CH3:1][C@@:2]1([OH:18])[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[CH:17]=[CH:16][C:14]([NH2:15])=[N:13][C:11]1=[O:12].C([Mg]Cl)(C)(C)C.Cl[P:26]([NH:36][C@H:37]([C:39]([O:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49]/[CH:50]=[CH:51]\[CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])=[O:40])[CH3:38])([O:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1)=[O:27]>C1COCC1>[Cl:35][C:32]1[CH:31]=[CH:30][C:29]([O:28][P:26]([NH:36][C@@H:37]([CH3:38])[C:39]([O:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49]/[CH:50]=[CH:51]\[CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])=[O:40])([O:9][CH2:8][C@H:5]2[O:4][C@@H:3]([N:10]3[CH:17]=[CH:16][C:14]([NH2:15])=[N:13][C:11]3=[O:12])[C@:2]([CH3:1])([OH:18])[C@@H:6]2[OH:7])=[O:27])=[CH:34][CH:33]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
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.
Workup
- customThe crude mixture was purified by column chromatography on silica gel (DCM:MeOH gradient from 90:10 to 80:20)
- dissolutionthe resulting solid was redissolved in DMSO
- custompurified by RP-HPLC
Sources & evidence
- ORD record
- ord-af64c2b412ac4bee8a27543fa9470758
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07879815B2
Reaction notes
Loading…