- One-Step Stereoselective Syntheses of C-Branched α-Deoxycyclitols from 1,6-Anhydrohexopyranoses
-
1,6-Anhydro-3,4-O-isopropylidene-β-D-galactopyranose (1) reacts with n-butyllithium to give exclusively 1D-1-C-butyl-2,3-O-isopropylidene-1,2,3,5/4-cyclohexanepentol (2a). 1,6-Anhydro-2,3-O-isopropylidene-β-D-mannopyranose (7) gives 1L-5-C-butyl-2,3-O-isopropylidene-1,2,3/4,5-cyclohexanepentol (8a) and 1L-1-C-butyl-3,4-O-isopropylidene-1,2,5/3,4-cyclohexanepentol (9a) as a by-product.Analogous reactions with methyllithium yield the corresponding C-methyl-branched deoxyinositols 2b, 4, 8b, and 9b.
- Klemer, Almuth,Kohla, Monika
-
p. 1662 - 1671
(2007/10/02)
-
- Photolytische Decarbonylierung von Anhydrozucker-Ulosen zur Synthese von 1,5-Anhydro-β-D-lyxo- und -ribofuranosen sowie 2,6-Anhydro-β-D-psicofuranosen
-
By photochemical decarbonylation of the 1,6-anhydro-2- (1) and -4-uloses (3) with D-lyxo configuration stereoselective ring contractions yield the 1,5-anhydro-β-D-lyxofuranose derivative 2.Via corresponding transformations the benzylidene derivative 9 is
- Heyns, Kurt,Neste, Helmut-Rainer,Thiem, Joachim
-
p. 891 - 908
(2007/10/02)
-
- HYDROGENOLYSIS OF BENZYLIDENE ACETALS OF 1,6-ANHYDRO-β-D-GALACTOPYRANOSE DERIVATIVES WITH THE LiAlH4-AlCl3 REAGENT
-
Benzylidenation of 1,6-anhydro-β-D-galactopyranose (1) and its 2-O-acetyl (2) and 2-O-allyl (3) derivatives under various conditions afforded mixtures of 1,6-anhydro-exo- and -endo-3,4-O-benzylidene-β-D-galactopyranose (4 and 5) and the 2-O-acetyl (6 and
- Subero, Carmen,Fillol, Luis,Martin-Lomas, Manuel
-
-