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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2205185Generated: October 27, 2026

Acetic Anhydride → (2R,3S,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-5-(difluoromethyl)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-tetrahydrofuran-3-yl acetate

https://huagongshe.com/reaction/2205185

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AnhydrideHCID 7918—
Reactant1-((2R,3S,4S,5R)-4-(Benzyloxy)-5-((benzyloxy)methyl)-5-(difluoromethyl)-3-hydroxytetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dioneHCID 118294339—
SolventPyridineHCID 1049—
Product(2R,3S,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-5-(difluoromethyl)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-tetrahydrofuran-3-yl acetateHCID 11829415788%

Reaction Conditions

Temperature20 °C

Reaction Steps

Ac2O (0.5 mL) was added into a solution of compound 34 (0.114 g, 0.24 mmol) in dry pyridine (4 mL). The reaction mixture was stirred at 20° C. for 3 h and then quenched by saturated aqueous NaHCO3 solution (2 mL). The organic phase was extracted with dichloromethane and then evaporated to dryness under reduced pressure. Purification by silica gel chromatography [petroleum ether:ethyl acetate (4:1)] afforded 35 (0.12 g, 88%) as a white solid. LC-MS: (M+H)+=517.2

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09370569B2
Source datasetuspto-grants-2016_06
ORD IDord-171eb1c8264748cfa0a082b7d911659e
Source noteuspto-grants-2016_06