Abstract: In the last decade, carbohydrates have attracted great
attention as renewable resources for the chemical industry.
Carbohydrates are abundantly found in nature in the form of
monomers, oligomers and polymers, or as components of
biopolymers and other naturally occurring substances. As natural
products, they play important roles in conferring certain physical,
chemical, and biological properties to their carrier molecules.The
synthesis of this particular carbohydrate glycomonomer is part of our
work to obtain biodegradable polymers. Our current paper describes
the synthesis and characterization of a novel carbohydrate
glycomonomer starting from D-glucose, in several synthesis steps,
that involve the protection/deprotection of the D-glucose ring via
acetylation, tritylation, then selective deprotection of the aromaticaliphatic
protective group, in order to obtain 1,2,3,4-tetra-O-acetyl-
6-O-allyl-β-D-glucopyranose. The glycomonomer was then obtained
by the allylation in drastic conditions of 1,2,3,4-tetra-O-acetyl-6-Oallyl-
β-D-glucopyranose with allylic alcohol in the presence of
stannic chloride, in methylene chloride, at room temperature. The
proposed structure of the glycomonomer, 2,3,4-tri-O-acetyl-1,6-di-
O-allyl-β-D-glucopyranose, was confirmed by FTIR, NMR and
HPLC-MS spectrometry. This glycomonomer will be further
submitted to copolymerization with certain acrylic or methacrylic
monomers in order to obtain competitive plastic materials for
applications in the biomedical field.
Abstract: The field of polymeric biomaterials is very important
from the socio-economical viewpoint. Synthetic carbohydrate
polymers are being increasingly investigated as biodegradable,
biocompatible and biorenewable materials. The aim of this study was
to synthesize and characterize some derivatives based on D-mannose.
D-mannose was chemically modified to obtain 1-O-allyl-2,3:5,6-di-
O-isopropylidene-D-mannofuranose and 1-O-(2-,3--epoxy-propyl)-
2,3:5,6-di-O-isopropylidene-D-mannofuranose.
The chemical structure of the resulting compounds was
characterized by FT-IR and NMR spectroscopy, and by HPLC-MS.