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Site Selectivity in the α-Silyl Lithiation of 3,4,6-Tris- O -( tert -butyldimethylsilyl)- d -glucal and 3,4-Bis- O -( tert -butyldimethylsilyl)- 6-deoxy- l -glucal with tert -Butyllithium

✍ Scribed by Friesen, Richard W.; Trimble, Laird A.


Book ID
118069570
Publisher
American Chemical Society
Year
1996
Tongue
English
Weight
137 KB
Volume
61
Category
Article
ISSN
0022-3263

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3,4-bis(O-tert-butyldimethylsilyl)-6-O-t
✍ Kirschning, Andreas 📂 Article 📅 1995 🏛 John Wiley and Sons 🌐 English ⚖ 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