Stereocontrolled Diels - Alder cycloadditions of sugar-derived dihydropyranones with dienes

2-Acetoxy-3,4-di-O-acetyl-D-arabinal (6), similar to its D-xylo analogue 4, reacted with benzyl alcohol by the tin(IV) chloride-promoted glycosylation to produce optically active (S)-2-benzyloxy-2H-pyran-3(6H)-one (8a). The L-arabinal derivative (5) gave 9a, the dihydropyranone enantiomer of 8a. The...

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Detalles Bibliográficos
Autores principales: Iriarte Capaccio, C.A., Varela, O.
Formato: JOUR
Materias:
Diastereoselectivity
Enantiomers
Addition reactions
Alcohols
Catalysts
Olefins
Stereochemistry
Synthesis (chemical)
Ketones
1,3 butadiene derivative
1,3 cyclohexadiene
2 acetoxy 3,4 di o acetyl dextro arabinal
2 benzyloxy 2h pyran 3(6h) one
2,3 dimethylbutadiene
alkadiene
arabinose derivative
cyclopentadiene derivative
dihydropyranone derivative
pyran derivative
tetrahydrobenzopyranone derivative
unclassified drug
article
catalysis
chirality
cycloaddition
enantiomer
optics
prediction
protein glycosylation
reaction analysis
stereochemistry
stereospecificity
synthesis
thermal analysis
Carbohydrates
Hydroxylation
Molecular Structure
Pyrones
Stereoisomerism
Temperature
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_00223263_v67_n22_p7839_IriarteCapaccio
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

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