By A. F. Bochkov
ISBN-10: 0080229492
ISBN-13: 9780080229492
Booklet by means of Bochkov, Aleksei Feodos Evich
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Sample text
V^R OH 43 chapters. Amongst v a r i o u s e x a m p l e s of g l y c o s y l a t i o n by t h e K o e n i g s - K n o r r r e a c t i o n t h e s y n t h e s e s o f o l i g o s a c c h a r i d e s , n a t u r a l g l y c o s i d e s ( s t e r o i d and t r i t e r p e n i c ) , and g l y c o s i d e s of a l i p h a t i c a l c o h o l s appear as the major area of a p p l i c a t i o n of t h i s method. G e n e r a l l y s p e a k i n g , t h e r e are no fundamental l i m i t a t i o n s f o r a l c o h o l i c a g l y c o n s undergoing g l y c o s y l a t i o n by t h e Koenigs-Knorr r e a c t i o n .
I n f a c t , e i t h e r 52^ o r 53^ a s i n t e r m e d i a t e s s h o u l d l e a d t o 1 , 2 t r o T t s - b r o m i d e 54^ o r ( a n d ) t o " 3 - i o n " 55^ a s a r e s u l t o f i n t e r a c t i o n w i t h b r o m i d e ion. A s f o r 1 , 2 - t i w i s - b r o m i d e l i k e 54^, i t i s d e f i n i t e l y k n o w n t h a t s u c h c o m p o u n d s r e a c t with a l c o h o l s w i t h r e t e n t i o n of c o n f i g u r a t i o n v i a acyloxonium ion (as 5 2 ) . AcOCH. AcO Br® 54 i^e CHjOAc ' — 0 OMe 'OAc AcC 28 Chemistry The same b e h a v i o u r scheme can p r e d i c t i n c r e a s e of h a l i d e of the 0-glycosidio Bond: Formation and Cleavage should obviously be expected for ion pair 55.
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^.
Chemistry of the O–Glycosidic Bond. Formation and Cleavage by A. F. Bochkov
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