The Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
87(6), P. 4154 - 4167
Published: March 3, 2022
The
reaction
of
a
series
anomeric
thioglycosides
with
various
glycosyl
acceptors
and
N-iodosuccinimide/catalytic
triflic
acid
was
investigated
respect
to
reactivity
selectivity.
In
general,
β-configured
donors
were
found
give
more
β-selective
outcome
compared
their
α-configured
counterparts.
relative
measured
through
competition
experiments,
the
following
order
established:
phenyl,
tolyl,
methyl,
ethyl,
isopropyl,
1-adamantyl.
Chemistry - A European Journal,
Journal Year:
2020,
Volume and Issue:
27(8), P. 2556 - 2568
Published: Sept. 17, 2020
Abstract
Chemical
synthesis
is
one
of
the
practical
approaches
to
access
carbohydrate‐based
natural
products
and
their
derivatives
with
high
quality
in
a
large
quantity.
However,
stereoselectivity
during
glycosylation
reaction
main
challenge
because
can
generate
both
α‐
β‐glycosides.
The
focus
present
article
concept
recent
mechanistic
studies
that
have
applied
statistical
analysis
quantitation
for
defining
stereoselective
changes
process.
Based
on
experimental
evidence,
detailed
discussion
associated
mechanism
degree
influence
affecting
outcome
included.
Angewandte Chemie International Edition,
Journal Year:
2021,
Volume and Issue:
61(6)
Published: Sept. 14, 2021
Abstract
The
stereoselective
introduction
of
the
glycosidic
bond
remains
one
main
challenges
in
carbohydrate
synthesis.
Characterizing
reactive
intermediates
this
reaction
is
key
to
develop
glycosylation
reactions.
Herein
we
report
characterization
low‐populated,
rapidly
equilibrating
mannosyl
dioxanium
ions
that
arise
from
participation
a
C‐3
acyl
group
using
chemical
exchange
saturation
transfer
(CEST)
NMR
spectroscopy.
Dioxanium
ion
structure
and
equilibration
kinetics
were
measured
under
relevant
conditions
highly
α‐selective
couplings
observed
suggesting
took
place
via
elusive
intermediate.
The Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
87(6), P. 4154 - 4167
Published: March 3, 2022
The
reaction
of
a
series
anomeric
thioglycosides
with
various
glycosyl
acceptors
and
N-iodosuccinimide/catalytic
triflic
acid
was
investigated
respect
to
reactivity
selectivity.
In
general,
β-configured
donors
were
found
give
more
β-selective
outcome
compared
their
α-configured
counterparts.
relative
measured
through
competition
experiments,
the
following
order
established:
phenyl,
tolyl,
methyl,
ethyl,
isopropyl,
1-adamantyl.
