BIBLIOS

  Ciências References Management System

Visitor Mode (Login)
Need help?


Back

Publication details

Document type
Book chapters


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

Participants in the publication
A. Matos (Author)
CQB - Centro de Química e Bioquímica 
R. Nunes (Author)
Dep. Química e Bioquímica
BIOISI - Instituto de Biossistemas e Ciências Integrativas
CQB - Centro de Química e Bioquímica 
C. Dias (Author)
A. P. Rauter (Author)
Dep. Química e Bioquímica
CQB - Centro de Química e Bioquímica 

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

Date of Publication
2017

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

Download

Export

APA
A. Matos, R. Nunes, C. Dias, A. P. Rauter, (2017). Cyclic acetals for regioselective protection in carbohydrate synthesis: A comparative experiment. Comprehensive Organic Chemistry Experiments for the Laboratory Classroom, 188-193

IEEE
A. Matos, R. Nunes, C. Dias, A. P. Rauter, "Cyclic acetals for regioselective protection in carbohydrate synthesis: A comparative experiment" in Comprehensive Organic Chemistry Experiments for the Laboratory Classroom, 2017, pp. 188-193

BIBTEX
@incollection{40229, author = {A. Matos and R. Nunes and C. Dias and A. P. Rauter}, title = {Cyclic acetals for regioselective protection in carbohydrate synthesis: A comparative experiment}, booktitle = {Comprehensive Organic Chemistry Experiments for the Laboratory Classroom}, year = 2017, pages = { 188-193}, address = {}, publisher = {Royal Society of Chemistry} }