By Walter A. & Derek Horton (eds.) Szarek
content material: The interplay among the ring-oxygen p-type lone pair and adjoining [sigma]-bonds in pyranose derivatives / Serge David --
The exo-anomeric influence / R.U. Lemieux, S. Koto, and D. Voisin --
Proton spin-lattice rest : a brand new, quantitative degree of aglycon-sugar interactions / J.M. Berry, L.D. corridor, D.G. Welder, and K.F. Wong --
The structural homes of the anomeric middle in pyranoses and pyranosides / G.A. Jeffrey --
points of conformational research of pentopyranosyl acetates, benzoates, and halides / Hans Paulsen, Peter Luger, and Fred R. Heiker --
The impression of reactant constitution and solvent on glycoside synthesis / Conrad Schuerch --
Conformational interactions in 1,4-heterobutane segments / Ernest L. Eliel and Eusebio Juaristi.
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And Watanabe, K. , Can J. , (1969) 47, 4427. 4. Berman, H. , Chu, S. S. , and Jeffrey, G. , Science, (1967) 157, 1576. 5. Jeffrey, G. , Pople, J. , (1972) 25, 117. 6. Delbaere, L. T. J. and James, M. N. , Department of Biochemistry, University of Alberta, unpublished results. 7. Lemieux, R. Y. Acad. , (1973) 222, 915. 8. Lemieux, R. , Nagabhushan, T. , Can. J. , (1972) 50, 773. 9. Delbaere, L. T. , James, M. N. , and Lemieux, R. , J. Am. Chem. , (1973) 95, 7866. 10. Reutov, O. A. and Shatkina, T.
RECEIVED September 27, 1978. ) Measure of Aglycon-Sugar Interactions (1) J. M. BERRY, L. D. HALL, D. G. WELDER, and K. F. ch003 Department of Chemistry, The University of British Columbia, Vancouver, British Columbia, Canada V6T 1W5 It is now well known that the anomeric effect of many substituents can dominate the conformations favoured by carbohydrate derivatives in solution. For example, all the pentopyransyl fluoride (2) and chloride derivatives (3) favour in solution that conformation in which the halogen substituent has an axial orientation - even in the case of the ß-D-xylopyranosyl derivatives where the C -chair conformation requires that all the substituents be axially oriented.
5°. T h u s , t h e r e c a n r e m a i n no d o u b t o f t h e i m p o r t a n c e o f t h e e x o a n o m e r i c e f f e c t t o t h e o r i e n t a t i o n o f an a g l y c o n . How i m p o r t a n t i s t h e d r i v i n g f o r c e i s t h e remaining problem. O b v i o u s l y , i f t h e e f f e c t i s i n t h e o r d e r o f 5 k c a l / m o l e , then i t would l i k e l y domi nate over a l l other f a c t o r s t h a t a r e l i k e l y t o i n f l u e n c e t h e t o r s i o n a p g l e d e f i n e d by 05 a n d t h e a g l y c o n i c c a r b o n , t h e s o c a l l e d