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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1694994Generated: November 1, 2026

Toluene → HCID 178455819, compound

https://huagongshe.com/reaction/1694994

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
ReactantTriphenylphosphineHCID 11776—
Reactantethyl N-ethoxycarbonyliminocarbamateHCID 220568—
ReactantN-{(S)-2-hydroxy-1-[(2S,4R)-4-methyl-5-oxotetrahydrofuran-2-yl]ethyl}-2-nitrobenzenesulfonamideHCID 66645672—
SolventTetrahydrofuranHCID 8028—
ProductHCID 178455819HCID 17845581992%

Reaction Steps

1.60 ml of a solution of diethyl azodicarboxylate in toluene (40%) (3.52 mmol) was added to a solution of 1.05 g of N-{(S)-2-hydroxy-1-[(2S,4R)-4-methyl-5-oxotetrahydrofuran-2-yl]ethyl}-2-nitrobenzenesulfonamide obtained in Example (106f) (2.93 mmol) and 923 mg of triphenylphosphine (3.52 mmol) in tetrahydrofuran (30 ml) under ice-cooling over five minutes, and the mixture was stirred at the same temperature for five minutes. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent: toluene/acetone=5/1) to obtain 916 mg of the title compound (yield: 92%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08158790B2
Source datasetuspto-grants-2012_04
ORD IDord-036a117069dc4949a11149e87d1c7b63
Source noteuspto-grants-2012_04