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Anomeric Effect. Origin and Consequences by Walter A. & Derek Horton (eds.) Szarek

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 impression / 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 --
facets of conformational research of pentopyranosyl acetates, benzoates, and halides / Hans Paulsen, Peter Luger, and Fred R. Heiker --
The effect 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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BERRY E T AL. ch003 890 -3 -1 (10 s e c ) ( 1 5 ) f o r t h e r i n g p r o t o n s o f t h e g a l a c t o p y r a n o s e r e s ­ i d u e c a n be f o r m u l a t e d i n t e r m s o f t h e v a r i o u s i n t e r p r o t o n p v a l u e s , a n d a s a r e s u l t o f t h e i n v e r s e s i x t h power d e p e n d e n c e on d i s t a n c e , we need o n l y c o n s i d e r n e a r e s t - n e i g h b o u r i n t e r a c t i o n s , namely gauche i n t e r a c t i o n s ( p ) , 1 , 3 - d i a x i a l i n t e r a c t i o n s ( p a , a ) and f o r t h e a n o m e r i c p r o t o n , t h e i n t e r - r i n g c o n t r i b u t i o n (p i n t e r r i n g ) ( s t r i c t l y we c a n n o t i g n o r e t h e v i c i n a l t r a n s - d i a x i a l i n t e r ­ a c t i o n s b u t i t i s s i m p l e r t o s o do f o r t h e p r e s e n t a r g u m e n t ) .

Thus replacement o f a p r o t o n by a d e u t e r i u m r e d u c e s t h e d i p o l e - d i p o l e r e l a x a t i o n c o n t r i b u t i o n f r o m t h a t s i t e t o c a . 6% o f i t s o r i g i n a l v a l u e . 1 1 1 c 2 c L e t us now s e e how t h i s e x p l i c i t r e l a t i o n s h i p , i n c o n j u n c t i o n w i t h t h e i n i t i a l n o n - s e l e c t i v e r e l a x a t i o n r a t e s , c a n be u s e d t o determine t h e c o n t r i b u t i o n which t h e methoxyl protons o f a methyl g l y c o s i d e make t o t h e r e l a x a t i o n o f t h e a n o m e r i c p r o t o n H - l .

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. , Tetrahedron, (1962) 18, 237. 11. Tardella, P. , Tetrahedron Letters, (1969) 14, 1117. 12. House, H. , Czuba, L. , and Olmstead, H. , J. Org. , (1969) 34, 2324. 13. Eliel, E. , Martin, R. J. , Org. , (1967) 47, 16. 14. Johnson, W. S. , J. Am. Chem. , (1947) 69, 1361. 15. , Bull. Soc. , France, (1950) 17, 631. 16. , Progr.

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