Dicyclohexylcarbodiimide → 5'-(N-CBz-L-valyl)-2',3'-dideoxy-3'-fluoroguanosine

Participants

Role	Name	HCID	Charge
Reactant	Dicyclohexylcarbodiimide	HCID 10868	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	N-Carbobenzoxy-L-valine	HCID 726987	—
Reactant	3'-Fluoro-2',3'-dideoxyguanosine	HCID 135431817	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Solvent	Dimethylformamide	HCID 6228	—
Product	5'-(N-CBz-L-valyl)-2',3'-dideoxy-3'-fluoroguanosine	HCID 136335655	—

Reaction Steps

To a solution of 2′,3′-dideoxy-3′-fluoroguanosine (810 mg, 3 mmole) and 4-dimethylaminopyridine (73 mg, 0.6 mmole), N-CBz-L-valine (1.5 g, 6 mmole) and 1-hydroxybenzotriazole (810 mg, 6 mmole) in DMF (20 ml) was added DCC (1.36 g, 6.6 mmole). After 72 h, the reaction mixture was filtered and concentrated in vacuo. 5′-(N-CBz-L-valyl)-2′,3′-dideoxy-3′-fluoroguanosine was isolated by silica gel column chromatography (1.15 g).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06974802B2
Source dataset	uspto-grants-2005_12
ORD ID	ord-7c486dc7bdd94a0eb5d47774ad77bc67
Source note	uspto-grants-2005_12