BIBLIOS

Tipo
Capítulo em Livro


Título
Cyclic acetals for regioselective protection in carbohydrate synthesis: A comparative experiment

Participantes na publicação
A. Matos (Author)
CQB
R. Nunes (Author)
Dep. Química e Bioquímica
BioISI
CQB
C. Dias (Author)
A. P. Rauter (Author)
Dep. Química e Bioquímica
CQB

Resumo
This multi-step synthetic route is based on the selective protection of methyl α-d-glucopyranoside at positions 4 and 6 with a benzylidene acetal, acetylation of the remaining free hydroxy groups and selective benzylidene acetal hydrolysis. This protocol illustrates the importance of the benzylidene acetal and of its hydrolysis for sugar regioselective manipulation. Comparison of the target compound’s NMR data with those of the peracetylated methyl α-d-glucopyranoside is the starting point for a valuable discussion on concepts such as multifunctionality, regioselectivity and the usefulness of acetal protecting groups in carbohydrate chemistry.

Editor
C A M Afonso, N R Candeias, D Pereira Simão, A F Trindade, J A S Coelho, B Tan, R Franzén


Instituição
FACULDADE DE CIÊNCIAS DA UNIVERSIDADE DE LISBOA

Suporte
Comprehensive Organic Chemistry Experiments for the Laboratory Classroom

Identificadores da Publicação
ISBN - 9781849739634

Editora
Royal Society of Chemistry



Keywords
column chromatography Carbohydrate Chemistry NMR regioselectivity cyclic acetal

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