Direct Protection of 1,2-Diols from α-Diketones

Synlett

Volumn 1996, Issue 8, 1996, Pages 793-795

  Douglas, Nina L ^a   Ley, Steven V ^a   Osborn, Helen M I ^a   Owen, Dafydd R ^a   Priepke, Henning W M ^a   Warriner, Stuart L ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542396822     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5523     Document Type: Article

References (9)

1. Grice P., Ley S. V., Pietruszka J., Priepke H. M. W. Angew. Chem. Int. Ed. Engl. 1996, 35, 197.
2. Ley S. V., Priepke H. W. M., Warriner S. L. Angew. Chem. Int. Ed. Engl. 1994, 33, 2290.
3. Grice P., Ley S. V., Pietruszka J., Priepke H. W. M., Walther E. P. E. Synlett 1995, 783.
4. Ley S. V., Priepke H. W. M. Angew. Chem. Int. Ed. Engl. 1994, 33, 2292.
5. Available from Avocado Research Chemicals Ltd., Shore Road, Port of Heysham Industrial Park, Heysham, Lancashire, LA3 2XY, Great Britain.
6. Montchamp J-L., Tian F., Hart M. E., Frost J. W. J. Org. Chem. 1996, 61, 3897.
7. +) 430.1628 found 430.1627.
8. After dihydroxylation a TFAA activated DMSO oxidation is used to install the α-diketone. See Amon C. M., Banwell M. G., Gravatt G. L. J. Org. Chem. 1987, 52, 4851.
9. 4) and concentrated in vacuo. The residue was chromatographed on silica gel, using ether/petrol (10:1) as eluent, to give 6-O-tert-butyldiphenylsilyl-α-D-glucopyranoside 13 (16.3mg, 71%) which was identical to the initial glucose derivative used.