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Amino derivatives of sucrose and α,α-trehalose. III. Preparation of 2-amino-2-deoxy- and 2,2'-diamino-2,2'-dideoxy derivatives

I. Ježo

Inst. Chem., Slovak Acad. Sci., Bratislava


Abstract: Tosylation of 6,6'-di-O-trityl-α,α-trehalose, followed by treatment with NaOMe gave 6,6'-di-O-trityl-2,3-anhydro-O-α-D-allopyranosyl-(1 → 1')-α-D-glucopyranoside (I). Treatment of I with PhCH2NH2 and Ac2O, followed by AcOH and then Ac2O in pyridine gave the α-D-altropyranosyl α-D-glucopyranoside deriv. (II; R = MeCO(PhCH2)N, R1 = MeCO). Treatment of I with MeOH and NH3 at 100°, followed by AcOH and HBr at 0° gave II (R = MeCONH, R1 = H). 6,6'-Di-O-trityl-3,3'-di-O-tosyl-α,α-trehalose reacted with NaOMe, followed by treatment with NH3 in MeOH at 100° in an autoclave for 8 hr and neutralization with HCl gave the α-D-altropyranosyl α-D-altropyranoside deriv. (III) dihydrochloride. D-Altrosamine hydrochloride was similarly prepd. from 3-O-tosyl-D-glucose.

Full paper in Portable Document Format: 273a381.pdf


Chemical Papers 27 (3) 381–386 (1973)

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