Acetylated 6‐iodo, 6‐bromo, 6‐chloro, and 6‐azido glucopyranosyl azides (IV) or (V) are obtained by nucleophilic displacement reactions of the tosylates (IIa) or (IIb), resp., which, in turn, are readily accessible from the anomeric azides (Ia), (Ib).

Carbohydrates U 0500 A Simple Method for the Preparation of Glycosyl Isothiocyanates. -The target compounds are prepared in one step from the corresponding peracetylated sugars and Me3SiNCS in the presence of SnCl4. -(KUEHNE, M.; GYOERGYDEAK, Z.; LINDHORST*, T. K.; Synthesis 2006, 6, 949-951; Inst. Org. Chem.,

Bei den früher als (IVa) bzw. (IVb) angesehenen Verbindungen handelt es sich tatsächlich um deren Anomere (IIc) bzw. (IIa), die ausgehend von der Mannopyranose (I) dargestellt werden (Zemplen‐Hydrolysierung von (IIa) gibt (IIb); nachfolgende Acetylierung gibt (IIc)).

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The reaction of the aldehydes (I) and L‐cysteine (II) affords the thiazolidines (III) as a diastereomeric mixture, which reacts diastereoselectively with Ac2O (IV) to give the cis‐acetyl derivatives (V).