Sucrose as chiral platform in the synthesis of macrocyclic receptor - Carbohydrate Chemistry: Chemical and Biological Approaches - page 236

Sucrose as chiral platform in the synthesis
of macrocyclic receptors
S " awomir Jarosz,* Mykhaylo A. Potopnyk and
Micha " Kowalski
DOI: 10.1039/9781849739986-00236
This review presents the syntheses of different analogs of sucrose. Transformations of this
di-saccharide at the terminal positions (C1 0 , or C6, or C6 0 ) provide modified sucroses such
as amines, uronic acids, thiols, or phosphorus derivatives. Preparation of so-called 'higher
sucroses' i.e. derivatives in which the terminal positions are elongated by a poly-
hydroxylated carbon chain is also reviewed. Special attention is directed to the synthesis
and properties of macrocyclic derivatives: crown- and aza-crown ethers with sucrose
scaffold. Such macrocyclic receptors exhibit interesting complexing properties towards
chiral ammonium salts.
1 Introduction
Sucrose (1; chemical name: b-D-fructofuranosyl a-D-glucopyranoside)
is the most available of all, low molecular weight carbohydrates. It is
produced from sugar cane and sugar beet in the scale of more than
150 mln tons per year; most of it is absorbed by food market. Still a
small percentage (but large quantity) of this disaccharide remains not-
consumed. The high overproduction of sucrose, being 'unused' at the
food market, is utilized in other fields. This disaccharide is a starting
material for the preparation of surfactants and liquid crystals containing
a sucrose backbone; also synthesis of bio-degradable polymers and chiral
synthons is of great interest. 1-5
Sucrose is the cheapest, chiral, optically pure material available on
the market. This relatively small molecule has nine stereogenic centers
(including two located at the anomeric positions). It possess also eight
hydroxyl groups (five secondary and three primary at the: C1 0 , C6, and
C6 0 ; carbon atoms of the glucose part are numbered C1-C6, while those of
fructose C1 0 -C6 0 ) which makes this compound almost insoluble in
organic solvents (except, to some extent: pyridine, DMF, DMSO). Because
of that, as well as of high complexity of the molecule, application of
sucrose as a 'typical' organic synthon is limited. Other limitation lays in
very high sensitivity of the glycosidic bond towards acids which is cleaved
completely within 30 min in 0.1% methanolic hydrogen chloride. 3
Although application of sucrose in 'normal' synthetic organic
chemistry is very demanding, this problem is of interest to several
industrial and/or scientific groups.
Transformations of sucrose may be carried out with destruction or
preservation of the carbohydrate backbone. Leading examples of the
former approach are shown in Scheme 1.