Cytidine → 2'-O-Nonylcytidine

HRID 1066421Notes

Reaction equation

HRID 1066421 reaction equation
[C@@H:1]1([N:10]2[CH:17]=[CH:16][C:14]([NH2:15])=[N:13][C:11]2=[O:12])[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3].[H-].[Na+].I[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>CN(C=O)C>[CH2:21]([O:3][C@@H:2]1[C@H:4]([OH:5])[C@@H:6]([CH2:7][OH:8])[O:9][C@H:1]1[N:10]1[CH:17]=[CH:16][C:14]([NH2:15])=[N:13][C:11]1=[O:12])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 6175CytidineHCID 202751-IodononaneHCID 24758Sodium hydride

Product 1

HCID 228683932'-O-Nonylcytidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cytidine (10.1 g, 0.0415 mol), sodium hydride (2.0 g, 1.2 eq), iodononane (9.8 ml, 1.2 eq.) in DMF (100 ml) were reacted as per the procedure of Example 71, Step 1 to yield the 2′ and 3′ isomers as a sticky foam (11.6 g).

Sources & evidence

ORD record
ord-633d6d91bf704fc58c5e7756e2fc06ce
Source dataset
uspto-grants-2001_06
Patent number
US06242592B1

Reaction notes

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