41356-09-6Relevant academic research and scientific papers
Bromination of sugar enones and enonolactones
Nardo, Christian Di,Varela, Oscar,Lederkremer, Rosa M. de,Baggio, Ricardo F.,Vega, Daniel R.,Garland, Maria T.
, p. 99 - 110 (2007/10/02)
Bromination of 2,4,6-tri-O-benzoyl-3-deoxy-D-erytro-hex-2-enono-1,5-lactone (1) took place diastereoselectively to afford a single product: 2,4,6-tri-O-benzoyl-2,3-dibromo-3-deoxy-D-altrono-1,5-lactone (2).The configuration of C-2 and C-3 was determined a
β-ELIMINATION IN ALDONOLACTONES. SYNTHESIS OF 2-DEOXY-D-lyxo-HEXOSE AND 2-DEOXY-d-arabino-HEXOSE
Sala, Luis F.,Cirelli, Alicia Fernandez,Lederkremer, Rosa M. De
, p. 61 - 66 (2007/10/02)
Benzoylation of D-glycero-L-manno-heptono-1,4-lactone (1) with benzoyl chloride and pyridine for 2 h afforded crystalline penta-O-benzoyl-D-glycero-L-manno-heptono-1,4-lactone (2), but a large excess of reagent during 8 h also led to 2,5,6,7-tetra-O-benzoyl-3-deoxy-D-lyxo-hept-2-enono-1,4-lactone (3).Catalytic hydrogenation of 3 was stereoselective and gave 2,5,6,7-tetra-O-benzoyl-3-deoxy-D-galacto-heptono-1,4-lactone (4).Debenzoylation of 4 followed by oxidative decarboxylation with ceric sulfate in aqueous sulfuric acid gave 2-deoxy-D-lyxo-hexose (5).Application of the same reaction to 3-deoxy-D-gluco-heptono-1,4-lactone afforded 2-deoxy-D-arabino-hexose (6).
