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Abstract
Methyl 6-amino-6-deoxy-α-D-glycopyranosides having the D-gluco, D-manno and D-galacto configurations (1a–3a), 2-aminoethanol (4a), 1-amino-1-deoxy-D-glucitol (5a), and 1-amino-1-deoxy-4-O-β-D-glucopyranosyl-D-glucitol (6a) were transformed into the corresponding per-O-acetyl amine hydrochlorides 1d–6d in excellent yields by using the 2,2-(diethoxycarbonyl)vinyl group for temporary amine protection. Deprotection of the peracetylated enamines 1c–6c was effected with chlorine in chloroform and no O→N acetyl migration occurred when short reaction times were used. Treatment of 1d–6d with thiophosgene resulted in the formation of peracetyl isothiocyanates (1e–6e).
Notes
The use of a 1:1.5 amine hydrochloride 1d-3d:thiophosgene molar ratio, previously found optimal for the synthesis of glycosyl isothiocyanates (see ref 8) resulted in concommitant O→N Acetyl migration particularly significant in the case of 3d.
