Triphenylphosphine → CID 66550531

Participants

Reaction Steps

In a 2.5 mL seal vial equipped with a stir bar was added (3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diol (150.00 mg; 0.60 mmol; 1.00 eq.) in tetrahydrofuran (2.00 ml) followed by triphenylphosphine (316.90 mg; 1.21 mmol; 2.00 eq.), isopropyl(Z)-(isopropoxyacetyl)diazenecarboxylate (0.25 ml; 1.21 mmol; 2.00 eq.). Diphenyl azidophosphate (0.26 ml; 1.21 mmol; 2.00 eq.) was then added dropwise in 15 min. During the addition, the former obtained green-yellow clear solution slowly turned to turbid and finally became clear again. The mixture was stirred at room temperature for 48 h. The mixture was purified via Yamazen channel 2 and lyophilized to provide 134.6 mg (81%) of the title compound as white solid.

Provenance & Evidence