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Homologation of Protected Monosaccharides at the Terminal Position with Grignard C1 Reagents

Zamojski A.

Polish Journal of Chemistry

2003

Vol. 77 / nr 3

257-281

The survey presents details of the recently introduced general method of homologation of monosaccharides. This method is based on chain-elongation of a protected monosaccharide from the terminal carbon atom. The terminal CH2OH group is oxidized to the aldehyde grouping and next reacted with an alkoxymethylmagnesium chloride (C1 Grignard) to form directly stereoisomeric homologues. The yields of the homologation products are high. Experiments aiming at improvement of the stereoselectivity of the reactions are described. The application of another C1 Grignard reagent, (phenyldimethylsilyl)methylmagnesium chloride, is presented. The advantages and disadvantages of the method are discussed. All syntheses connected with the important bacterial heptose, L-glycero-D-manno-heptose and its oligosaccharides are described.