Communications Chemistry,
Journal Year:
2025,
Volume and Issue:
8(1)
Published: March 7, 2025
The
stereoselective
introduction
of
glycosidic
bonds
is
one
the
greatest
challenges
in
carbohydrate
chemistry.
A
key
aspect
controlling
glycan
synthesis
glycosylation
reaction
which
linkages
are
formed.
outcome
governed
by
a
reactive
sugar
intermediate
-
glycosyl
cation.
Glycosyl
cations
highly
unstable
and
short-lived,
making
them
difficult
to
study
using
established
analytical
tools.
However,
mass-spectrometry-based
techniques
perfectly
suited
unravel
structure
gas
phase.
main
approach
involves
isolating
intermediate,
free
from
external
influences
such
as
solvents
promoters.
Isolation
allows
examining
their
integrating
orthogonal
spectrometric
spectroscopic
technologies.
In
this
perspective,
recent
achievements
gas-phase
research
on
highlighted.
It
provides
an
overview
used
probe
methods
for
interpreting
spectra.
connections
between
data
mechanisms
solution
explored,
given
that
reactions
typically
performed
solution.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: March 24, 2025
The
stereoselective
synthesis
of
nucleotide
diphosphate
(NDP)
uronic
acids
from
simple
sugar
precursors,
including
d-gluco-,
d-galacto-,
and
d-mannopyranoside
derivatives,
is
described.
Key
to
this
convergent
the
coupling
unprotected
acid
1-phosphate
with
a
phosphorimidazolide
directly
form
NDP-uronic
acid,
which
11
derivatives
were
prepared.
compatible
carboxylic
functionality
present
in
acid-1-phosphates,
conversions
>95%
isolated
yields
typically
above
60%.
features
work
include
(i)
α-d-phosphoglycosides
perbenzylated
α-
β-d-thioglycosides,
(ii)
selective
mild
oxidation
galactose-,
glucose-,
mannose-1-phosphates
corresponding
acid-1-phosphate,
(iii)
conditions
provide
acid-1-phosphates
phosphorimidazolides.
This
chemistry
currently
use
develop
inhibitors
key
enzymes
involved
antibiotic
resistance.
Journal of the American Chemical Society,
Journal Year:
2025,
Volume and Issue:
unknown
Published: March 31, 2025
We
herein
reported
a
catalytic,
minimally
protected,
and
highly
α-stereoselective
glycosylation
protocol
using
carboxylic
acid
as
an
acceptor
glycosyl
8-alkynyl-1-naphthoate
donor,
enabling
efficient
access
to
unprotected
α-1-O-
2-O-acyl
glycosides.
This
method
demonstrates
excellent
functional
compatibility
scope
generality,
allowing
for
the
of
wide
range
complex
acids.
Notably,
we
successfully
synthesized
two
natural
products,
α-penta-O-galloyl-d-glucopyranose
nyctanthesin
A,
this
protocol.
Mechanistic
studies
highlighted
crucial
role
1-O
ester
functionality
in
ensuring
chemoselectivity
important
contribution
2-O
facilitating
reaction.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: May 5, 2025
Reported
herein
is
the
expansion
of
cooperatively
catalyzed
Koenigs-Knorr
glycosylation
reaction,
known
as
"the
4K
reaction".
It
has
recently
been
discovered
that
thioglycosides
can
be
activated
in
presence
molecular
iodine,
a
metal
salt,
and
an
acid
additive.
The
mechanistic
studies
proposed
interaction
anomeric
sulfur
with
thiophilic
iodine.
resulting
complex
stable
until
halophilic
silver
salt
additive
are
added.
This
discovery
opened
new
avenue
for
development
promoters
do
not
activate
absence
Presented
bismuth(III)
triflate
efficient
activator
via
reaction
pathway.
