Cytidine → 2'-O-Nonylcytidine

HRID 368727Notes

Reaction equation

HRID 368727 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-f45fe0de1f704c428b0d60062018bdb3
Source dataset
uspto-grants-2000_10
Patent number
US06133438

Reaction notes

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