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135 e d w i t h good s e l e c t i v i t y . 1 3 6 Suitably protected phenylthio glycosides t r e a t e d with dialkyl Both z i n c s i n d i - i o d o m e t h a n e o f f e r a new r o u t e t o C - g l y c o s i d e s . a- a n d B-D-glucopyranose compounds g a v e p r o d u c t s w i t h a 3:l a : B P h e n y l t h i o g l y c o s i d e s c a n b e u s e d to g i v e m a l o n i c a c i d r a t i o . 137 C - g l y c o s i d e s (Scheme 18). )~; G , R o n y NL S c h e m e 18 S e v e r a l approaches t o C-glycosides have used alkenes produced from a l d o s e s by W i t t i g or r e l a t e d p r o c e d u r e s .

31 3: Clycosides and Disaccharides ;L + @ AAcO (& AcO Me Me R-ehts, L, BF3 t R S L R ~ R = Me- 5 i Me3 e S i M e 3 R= 3 1 : - 1 1 . 7 3 Me R= +SLDuC Me Ph, Scheme 20 -____ A c-o ~ Me c " " The f i r s t C l a i s e n r e a r r a n g e m e n t o f t h e p a i r shown i n Scheme 2 2 i s much t h e f a s t e r , and t h e p r o c e s s e s c a n t h e r e f c r e b e u s e d t o make 2-enes or 3-enes i n t h i s s e r i e s . The r a t e d i f f e r e n c e , which was ___f R = SL Bu'Me, Scheme 22 n o t o b s e r v a b l e w i t h c y c l o h e x e n e d e r i v a t i v e s , was a s c r i b e d t o t h e w e a k e n i n g o f t h e C-3-0 bond by a " v i n y l o g o u s a n o m e r i c e f f e c t " .

The following trisaccharides having D-glucose at the reducing termini have been synthesized (the first twc B-linked to ceramide) : g-a-C-Galp-( 1+4)-g-B-D-Galp-B-D0-a-0-Galp-( 1+3)-g-B-D-Galp-B-D-Glc," O-@-D-GlcpUA-(l+Q)Glc ,I1 B-D-Galg-D-Glc, (a Klebsiella po1;ysaccharide constituent) ,I2 O-a-DNeug5Ac-(2+6)-g-B-D-Galp-(1+4)-D-Glc (present in human milk), 15 O - ~ - D - N ~ L I ~ ~ A C - (-~ + ~ ) - O - B - D - G ~ ~ ~ - ( ~(part + ~ ) -of D - aG ~ganglioside C 14chain). The following o t h e r hexose-terminating trimers have also been reported: O-B-D-GaipNAc-(1+4)-g-~-D-GlcpNAc-(l-+2)-D-Man (and the 4"-sulphate) ,I5 g-a-D-Manp-( 1+2)-g-a-D-Manp-( 1 q )-D-Gal and O-a-D-Manp-(1-+2)-g-B-D-Manp-(l+3)-D-Gal.

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