Document type
Book chapters
Title
Cyclic acetals for regioselective protection in carbohydrate synthesis: A comparative experiment
Participants in the publication
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
Summary
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(s)
C A M Afonso, N R Candeias, D Pereira Simão, A F Trindade, J A S Coelho, B Tan, R Franzén
Institution
FACULDADE DE CIÊNCIAS DA UNIVERSIDADE DE LISBOA
Where published
Comprehensive Organic Chemistry Experiments for the Laboratory Classroom
Publication Identifiers
ISBN - 9781849739634
Publisher
Royal Society of Chemistry
Edition
1st
Number
chapter 3.1.17
Number of pages
6
Starting page
188
Last page
193
Keywords
column chromatography
Carbohydrate Chemistry
NMR
regioselectivity
cyclic acetal
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