By R J Ferrier; Regine Blattner; Royal Society of Chemistry (Great Britain); et al
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Extra resources for Carbohydrate chemistry : monosaccharides, disaccharides and specific oligosaccharides
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Carbohydrate alcohols, 88% of 1,6-linked glucobiosides being produced with a,p-ratio 1:3. 26 A striking stereochemical factor was discovered when tetra-~-acetyl-D-glucopyranose was coupled with ally1 bromide in the presence of sodium hydride in dichloromethane. Under these conditions the P-glycoside was produced; however, when tetrabutylammonium iodide was added the a, p-ratio swung dramatically to 98:2. 27 It has now been shown that 0-protection of the donor is not required for the generation of glycosyl donors and that free sugars in DMF with sodium hydride present react directly with 4-substituted benzyl bromides, the glycosidic products being separated by column chromatography.
163 DIBALH reduction of tetra-0-benzyl-D-gluconoI $lactone ethylene acetal affords the 2-hydroxyethyl P-glycoside with high selectivity and good yield. 165 Cellobiose has also been linked 3: Glycosidesand Disaccharides 31 OBn OJ 44 by way of glycosylamine bonding to a peptide,166and maltose by use of the 2bromoethyl-O-acetylated glycoside has been bonded to the porphyrin benzochlorin. 3:l to 1:9 by alteration in the activation and condensation conditions. 168 In closely related work a very interesting experiment was done which tested O-benzyl compounds against O-benzoyl compounds in the tetramethyl phosphoroamidate series.