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Observation of .alpha.-silyl carbanions in the metalation of 3,4,6-tri-O-(tert-butyldimethylsilyl)-D-glucal

✍ Scribed by Friesen, Richard W.; Sturino, Claudio F.; Daljeet, Anand K.; Kolaczewska, Aleksandra


Book ID
126094094
Publisher
American Chemical Society
Year
1991
Tongue
English
Weight
604 KB
Volume
56
Category
Article
ISSN
0022-3263

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3,4-bis(O-tert-butyldimethylsilyl)-6-O-t
✍ Kirschning, Andreas πŸ“‚ Article πŸ“… 1995 πŸ› John Wiley and Sons 🌐 English βš– 366 KB

## Abstract The reaction of 3,4‐bis(__O__‐__tert__‐butyldimethylsilyl)‐6‐__O__‐tosyl‐D‐glucal 4 with the Koser reagent [PhI(OH)OTs] unexpectedly afforded tetrahydrofurfural 6 as well as 2,3‐anhydropyranose 7 as major products. This unprecedented, stereoselective transformation helps to gain further