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

By A. F. Bochkov

Ebook by way of Bochkov, Aleksei Feodos Evich

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

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C a n b e made a g a i n s t 105 the corresponding mechanistic proposi­ 40 Chemistry in the nresence tion. of of the O-glyoosidio Bond: the deuterated methanol Formation that this and Cleavage reaction precedes A l t e r n a t i v e l y , the r e l a t i v e l y slow i r r e v e r s i b l e r e a c t i o n on t h e g l y c o s i d i c c e n t r e o f i o n 1 0 4 , w h i c h g i v e s r i s e t o stereospecifically. ^^^) b e l i e v e t h a t t h e c o u p l i n g o f i o n 1 0 4 w i t h a n a l c o ­ hol i s the r a t e - d e t e r m i n i n g s t a g e i n g l y c o s y l a t i o n , at l e a s t for i s o m e r i z a t i o n of o r t h o e s t e r 95^ i n c h l o r o b e n z e n e .

3 . and 2 . 5 . 1 . ) . However, such a s i m p l i f i e d interpreta­ t i o n l e a v e s many u n s o l v e d p r o b l e m s a n d n o a n s w e r t o many q u e s t i o n s t h a t a r e i m p o r t a n t from t h e v i e w p o i n t o f b o t h t h e o r y and s y n t h e t i c p r a c t i c e . Obviously a g e n e r a l and d e t a i l e d m e c h a n i s t i c scheme of t h i s r e a c t i o n must e x p l a i n t h e main r e g u l a r i t i e s o f t h e i n f l u e n c e o f a c c e p t o r t y p e , t h e n a t u r e of t h e s o l v e n t , and t h e s t r u c t u r e and s t e r e o c h e m i s t r y o f a c y l g l y c o s y l h a l i d e and a g l y c o n f e a t u r e s on t h e r a t e s o f t h e m a i n and s i d e r e a c t i o n s .

T h e i n t e r c o n v e r s i o n of o r t h o e s t e r s 79^ and 8 2 , i s c a t a l y s e d by v a r i o u s a c i d i c a g e n t s . I t u s u a l l y proceeds r e a d i l y , 2 2 3 - 2 2 5 sometimes even w i t h ­ o u t a c a t a l y s t . ^ ^ ^ » ^ ^ 7 The c a t a l y s t s of b o t h d i r e c t and i n d i r e c t g l y c o s y l a t i o n , i , e , t h e two r e a c t i o n s l e a d i n g from 79 + 80^ t o 8 1 , a r e more p e c u l i a r : t h e y c a n promote r e - e s t e r i f i c a t i o n as well,2283229 Therefore i n o r d i n a r y r e a c t i o n m i x t u r e s of o r t h o e s t e r g l y c o s y l a t i o n , g l y c o s i d e f o r m a t i o n c a n f o l l o w b o t h p o s s i b l e p a t h w a y s simultaneously.

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