Carbohydrate chemistry : monosaccharides, disaccharides and by R J Ferrier; Regine Blattner; Royal Society of Chemistry

By R J Ferrier; Regine Blattner; Royal Society of Chemistry (Great Britain); et al

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M. Gange, Glycoconj. , 1997, 14, 501. J. G. D. French, Carbohydr. , 1997,298, 1. N. Whitfield, Tetrahedron, 1997,53, 11493. A. , 1997,8,2727. P. S. Shalamai, Biopolim. Kleta, 1996, 12, 86 (Chem. , 1997,126,238 547). L. Kramer and E. Steckhan, Tetrahedron, 1997,53, 14645. R. I. Leon, P. Moreno and E. Suarez, J. Org. , 1997, 62, 8974. A. Djurendic, S. Velimirovic, M. Popsavin, V. Popsavin and D. Miljkovic, J. Serb. Chem. , 1997,62, 393 (Chem. , 1997, 127,34 417). K. Kasbeck and H. Kessler, Liebigs Ann.

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.

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