Among the steric and stereoelectronic effects exhibited by saturated six-membered hydroxylated heterocycles, the anomeric, exo-anomeric and inverse anomeric effects have been widely studied. It is well established that polar groups (OH, OR, halogens, etc.) at the glycosidic position usually adopt an axial arrangement (anomeric effect), which contrasts with amino functionalities preferring an equatorial disposition (inverse anomeric effect).1 The anomeric behavior of both isocyanate and isothiocyanate groups, often described as "pseudohalogens", has been scarcely studied. To bridge this gap, we have synthesized and evaluated in detail a and p anomers of 2,3,4-th-O-acetyl-D-xylopyranosyl isothiocyanate (7, 8) according to the scheme outlined below.
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