Hydrochloric Acid → HCID 86734704, compound

Participants

Reaction Steps

One gram of daunosamine (II) hydrochloride was suspended in anhydrous diethyl ether and treated at 0° C. with 8 ml. of trifluoroacetic anhydride. After allowing the suspension to stand for two hours at 0° C. and one hour at room temperature, the solvent was removed under reduced pressure and the residue was crystallized from dichloromethane to yield 1.1 g. of 2,3,6-trideoxy-1-trifluoroacetoxy-3-trifluoroacetamido-4-trifluoroacetoxy-L-lyxopyranose (IIA), having a m.p. of 132°-134° C. and a mass spectrum m/e 391 (M-44), 322 (M-113). 0.5 g of (IIA) in anhydrous diethyl ether was treated at 0° C. with anhydrous gaseous hydrogen chloride. After standing at +5° C. overnight, the solvent was removed in vacuo to yield 1-chloro-2,3,6-trideoxy-3-trifluoroacetamido-4-trifluoroacetoxy-α-L-lyxohexopyranose (IIB) as crystalline product. The NMR spectrum of (IIB) in CDCl3 was as follows:

Provenance & Evidence