By John L. Hickson

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Treatment o f s u c r o s e w i t h a b o u t t w o m o l a r e q u i v a l e n t s o f £-toluenes u l f o n y l c h l o r i d e i n p y r i d i n e f o r 6 days a t 0 ° a f t e r chromatography on s i l i c a g e l , gave c r y s t a l l i n e 6 , 6 ' - d i O - p - t o l y l s u l f o n y l s u c r o s e ( L ) i n 1 8 % y i e l d (26). A s i m i l a r r e a c t i o n o f sucrose w i t h t h r e e moles o f p - t o l u e n e s u l f o n y l c h l o r i d e a n d p y r i d i n e g a v e 1',6,6 -tri-0-£t o l y l s u l f o n y l s u c r o s e (M) i n 2 3 % y i e l d (22) .

20031 ACS Symposium Series; American Society: Washington, DC, 1977. 48 SUCROCHEMISTRY o x y g r o u p a t C-6 i s m o r e r e a c t i v e t h a n t h e s u l f o n y l o x y g r o u p C-6'. A similar difference i n the r e a c t i v i t i e s o f t h e s u l f o n y l o x y g r o u p s a t C - l a n d C-4 i n (S) a l s o h a s b e e n e s t a b l i s h e d (37). Compound ( S ) , o n r e a c t i n g w i t h s o d i u m a z i d e i n hexamethylphosphorTc t r i a m i d e f o r 16 h r s . a t 85°,gave 6 - a z i d o - 6 - d e o x y - l , 3 , 4 - t r i - 0 - ( m e t h y l s u l f onylhß-]>-f r u c t o f u r a n o s y l 4 , 6 - d i a z i d o - 4 , 6 - d i d e o x y 2 , 3 - d i - 0 - ( m e t h y l s u l f o n y l ) - a - D - g a l a c t o p y r a n o s i d e (U) i n 80% y i e l d .

H a l l , L . D . , Steiner, P . R . , and Pedersen, C . , Can. J . , (1970), 48, 1155. F a r r a r , T . C . , and Becker, E . D . , "Pulse and Fourier Transform N . M . R . " , Academic Press, New York, N . Y . , 1971. Cooley, J . W . , (1965), 19, 297. Bock, K . , and Pedersen, C . Chem. Soc. Perkin II, (1974), 293. H a l l , L . D . Am. Chem. S o c . , (1976), 98, 1269. Bock, K . , and H a l l , L . D . , Carbohydr. , (1975), 40, C3. Preston, C . M . , and H a l l , L . D . , Chem. Comm. (1972), 1319.

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