By D. R. Bundle, G. Descotes, J. Gigg, R. Gigg, W. Klaffke, B. Meyer, J. Staněk, T. Suami, J. Thiem (auth.)
Contents: D.R. package deal, Ottawa, Ont., Canada: Synthesis of Oligosaccharides concerning Bacterial O-AntigensG. Descotes, Villeurbanne, France: Synthetic Saccharide PhotochemistryJ. Gigg, R. Gigg, London, united kingdom: Synthesis of GlycolipidsB. Meyer, Athens, GA, united states: Conformational features of OligosaccharidesJ. Stanek, Jr., Prague, CSFR: Preparation ofSelectively Alkylated Saccharides as artificial IntermediatesT. Suami, Tokyo, Japan: Chemistry of Pseudo-SugarsJ. Thiem, W. Klaffke, Hamburg, FRG: Syntheses of Deoxy Oligosaccharides
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60 60 60 61 62 62 5 Photoreduction and Photoxidation Reactions of Sugars . . . . . 1 P h o t o r e d u c t i o n . . . . . . . . . . . . . 1 P h o t o d e o x y g e n a t i o n . . . . . . . . . . 1. I. 1 A c e t a t e s . . . . . . . . . . . 2 P i v a l o a t e s . . . . . . . . . . . 3 B e n z o a t e s . . . . . . . . . 5. I. 4 T r i f l u o r o m e t h a n e S u l f o n a t e s , T h i o c a r b a m a t e s a n d Xanthates . . . . .
The corresponding radical is supposed to be more planar than pyramidal to explain the lower degree of stereoselectivity for the reduction process of 8b into 9. 3sn01 AIBN AcO--~_-0 AcO-'~ AcO D 0 AcO AcO H inversion 9 0 % ^ AcO O retention 60% lO fost hv retention 90°/° 9 lO Scheme 4 carbon-carbon bond coupling according to Scheme 5. This photosubstitution occurs with ~-bromo or 13-phenylselenosugars 11 and 12 to give 13 with a similar stereoselectivity in favour of the axial arrangement of the C-glycosidic bond [I 8, 19].
V. light or NBS yields 2-O-benzoyl glycosylbromides which may be converted in situ to glycosides and disaccharides in good yields (Scheme 2). These reaction conditions are compatible with protective groups like esters (acetates, benzoates, tosylates) and silyl ethers. 2 Carbon-Oxygen Bond Formation The anomeric hydrogen abstraction can be obtained by an intramolecular "Barton type" reaction rising hydroxyalkylglycosides in presence of iodine and mercury oxide under irradiation. This methodology, is used for the synthesis of anomeric spiroorthoesters [6 and 7 in scheme 3).