De novo asymmetric synthesis of anthrax tetrasaccharide and related tetrasaccharide
(Chemical Equation Presented) A de novo asymmetric approach to the natural product anthrax tetrasaccharide 1 and an analogue 2 with an anomeric hexyl azide group has been developed from acetylfuran. The construction of the tetrasaccharide was achieved by
Guo, Haibing,O'Doherty, George A.
p. 5211 - 5220
(2008/12/21)
SYNTHESIS OF (L)-DAUNOSAMINE AND RELATED AMINO SUGARS
1-(2-Furyl)ethanol (6) has been converted into methyl (+/-)-daunosaminide (1) and methyl (+/-)-ristosaminide (3) by use of an intramolecular cyclisation of a trichloroacetimidate group. (+/-)-Daunosamine (1) has been obtained more directly from the alcohol (10) by use of a modified Mitsunobu reaction; the scope of the latter reaction has been explored using cyclohex-2-en-1-ol as a model substrate.Asymmetric reduction of 2-acetylfuran (5) has given (S)-1-(2-furyl)ethanol (46) in good enantiomeric excess, thus providing a short route to the L-enantiomers of the amino sugars (1), (2), and (3) from a cheap, non-carbohydrate precursor.
Sammes, Peter G.,Thetford, Dean
p. 111 - 124
(2007/10/02)
Direkte Synthese von ungesaettigten Kohlenhydraten und Cycliten aus Oxiranen
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Paulsen, Hans,Heiker, Fred R.,Feldmann, John,Heyns, Kurt
p. 636 - 638
(2007/10/02)
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