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Chemistry of the O–Glycosidic Bond. Formation and Cleavage by A. F. Bochkov

By A. F. Bochkov

Publication by means of Bochkov, Aleksei Feodos Evich

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Chemistry of the O–Glycosidic Bond. Formation and Cleavage

Publication by means of Bochkov, Aleksei Feodos Evich

Additional resources for Chemistry of the O–Glycosidic Bond. Formation and Cleavage

Example text

1 . ) , are d i s c u s s e d here for the example of a D - g l u c o s y l c h l o r i d e 5 0 . The f i r s t i n c l u d e s t h e f a s t i s o m e r i z a t i o n o f g l y c o s y l - c a t i o n 51_ i n i t i a l l y f o r m e d t o a c y l o x o n i u m i o n 52^ w i t h t h e following standard path to 1,2-trans-glycoside. The o t h e r i s b a s e d o n t h e c o n c e p t o f an i n t i m a t e i o n p a i r w i t h a d e f i n i t e s t e r e o c h e m i s t r y ( i . e . w i t h t h e arrangement of a counter i o n on one d e f i n i t e s i d e of a carbonium i o n ) , which provides s t e r e o s p e c i f i c i t y of t h e f o l l o w i n g a t t a c k by n u c l e o p h i l e s .

Most of t h e s e o b s e r v a t i o n s w e r e r a t i o n a l i z e d b y t h e d i s c o v e r y of a n o t h e r g l y ­ c o s y l a t i o n r e a c t i o n between o r t h o e s t e r s and a l c o h o l s which l e a d s a l m o s t s t e r e o ­ s p e c i f i c a l l y t o a l , 2 - c ^ . « 9 - g l y c o s i d e w i t h f r e e h y d r o x y l g r o u p a t C-2 88 and a l k y l a c e t a t e 89 e l i m i n a t i o n . » ^ " ^ ^ T h e r e a c t i o n was d i s c o v e r e d and s t u d i e d i n d e t a i l f o r g l u c o s e o r t h o a c e t a t e e x a m p l e s 87^.

T h e r e f o r e , a n y d e t a i l e d m e c h a n i s m s h o u l d i n c l u d e p a r t i c i p a t i o n o f t h e 1-0a c y l group i n t h e r e a c t i o n a t C - 1 . ^^^^ The r e a c t i o n was shown t o b e c e r t a i n l y f i r s t i n k i n e t i c o r d e r f o r b o t h bromide and m e r c u r y ( I I ) c y a n i d e and zero o r d e r f o r t h e a l c o h o l . I t was shown, i n a d d i t i o n , t h a t i n t h e same s y s t e m , b u t b u f f e r e d w i t h m e r c u r y ( I I ) o x i d e , t h e o r t h o e s t e r and l,2-tra7is-glucoside a r e accumulated i n a l m o s t equal amounts.

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