Carbohydrate Research p. 293 - 303 (1997)
Update date:2022-07-29
Topics:
Lichtenthaler, Frieder W.
Klaeres, Ulrich
Szurmai, Zoltan
Werner, Bernd
A concise practical, large scale-adaptable six-step sequence has been developed for the transformation of diacetone-glucose into 4,6-di-O-benzoyl- 3-O-benzyl-α-D-arabino-hexo-pyranos-2-ulosyl bromide (7), a most useful indirect β-D-mannosyl donor as its blocking group pattern allows the construction of biologically relevant β-D-mannosides branched at O-3 and O- 6. The broad utility of this new ulosyl bromide 7 resides in its high anomeric reactivity, and in the ease and uniformity with which β- stereocontrol can be achieved over both, glycosidations and carbonyl reduction of the β-ulosides formed: Koenigs-Knorr conditions exclusively provide β-glycosiduloses, hydride reduction of their carbonyl functions proceeds with high stereoselectivities (> 20:1) in favor of the β-D- mannosides. These preparatively auspicious properties are materialized in an efficient, straightforward synthesis of α-D-Manp-(1 → 6)-[α-D-Manp-(1 → 3)]-β-D-Manp-(1 → O)-Octyl, the 3,6-O-branched core-mannotrioside carrying an octyl spacer instead of the chitobiosyl unit.
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